Awesome and Easy Science Experiments about Dihydro-2H-pyran-2,6(3H)-dione

Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions. you can also check out more blogs about 108-55-4. Formula: C5H6O3.

Children learn through play, and they learn more than adults might expect. Science experiments are a great way to spark their curiosity, Formula: C5H6O3108-55-4, Name is Dihydro-2H-pyran-2,6(3H)-dione, SMILES is O=C1CCCC(O1)=O, belongs to Tetrahydropyrans compound. In a article, author is Popa, Adriana, introduce new discover of the category.

Thermal behavior of aminotrimethoxysilanphosphonate functionalized onto styrene-divinylbenzene copolymer

The chlorometylated styrene-divinylbenzene copolymer with different percent of divinylbenzene (code: S-6.7 DVB, S-12DVB, and S-15DVB) was functionalized with 3-hydroxybenzaldehyde for obtaining intermediated polymers. The aminotrimethoxysilanphosphonate groups were grafted by one-pot reactions in tetrahydrofuran using three components: polymers grafted with aldehyde groups (code: CHO-6.7, CHO-12, and CHO-15), 3-aminopropyltrimethoxysilane, diethylphosphite. The aminotrimethoxysilanphosphonate groups functionalized onto styrene-(6.7, 12, and 15%) divinylbenzene copolymer (code: PAF-6.7, PAF-12, and PAF-15) and evolution of the reaction were evidenced by FT-IR spectroscopy and porous structure by N(2)adsorption-desorption, SEM microscopy. The thermal behavior of aldehydes and materials: PAF-6.7, PAF-12, and PAF-15 are different than initial polymer supports.

Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions. you can also check out more blogs about 108-55-4. Formula: C5H6O3.

Reference:
Tetrahydropyran – Wikipedia,
,Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 108-55-4

108-55-4, As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A flask was charged with AlCl3 (96.38 mmol, 12.85 g, 2.2 equiv) and dry benzene (20 ml) under calcium chloride guard tube and the formed suspension was stirred on ice bath. Subsequently, a solution of glutaric anhydride 10 (43.8 mmol, 5.00 g) in dry benzene (40 ml) was added dropwise over 30 minutes (t < 8 C). The cooling bath was removed and the resulting mixture was stirred at room temperature for 19 hours. The mixture was carefully quenched with water (95 ml) and conc. H2SO4 (10 ml), the aqueous layer was extracted with ethyl acetate (1 x 200 ml, 3 x 50 ml), the combined organics were dried over Na2SO4, filtered and concentrated. The crude product was crystallized from ethyl acetate to yield 5-oxo-5-phenylpentanoic acid (7.00 g, 83%) as a yellow-brown powder;1 mp 124-125 C; 1H NMR (300 MHz, acetone-d6): delta = 1.99 (m, 2H), 2.44 (t, J = 7.2 Hz, 2H), 3.13 (t, J = 7.2 Hz, 2H), 7.51 (m, 2H), 7.62 (m, 1H), 8.01 (d, J = 7.8 Hz, 2H), 10.56 (bs, 1H). 5-Oxo-5-phenylpentanoic acid (26.1 mmol, 5.02 g), paraformaldehyde (78.3 mmol, 2.35 g, 3.0 equiv) and piperidine (5.3 mmol, 0.52 ml, 0.2 equiv) were dissolved/suspended in pyridine (22 ml) and stirred at 70 C for 21 hours. Afterwards, the mixture was poured into 3M H2SO4 (100 ml), the aqueous layer was extracted with ethyl acetate (3 x 100 ml), the combined organics were dried over Na2SO4, filtered and concentrated. The residue was redissolved in CH2Cl2 (100 ml) and extracted with a mixture of half-saturated aqueous NaHCO3 (300 ml) and 2M NaOH (20 ml). The extraction was repeated with half-saturated aqueous NaHCO3 (50 ml). The combined aqueous solutions were washed with CH2Cl2 (2 x 50 ml) and afterwards acidified with conc. H2SO4 to pH = 1-2 and extracted with ethyl acetate (1 x 100 ml, 3 x 70 ml). The combined organics were dried over Na2SO4, filtered and concentrated to give 4-benzoylpent-4-enoic acid 9a (4.60 g, 86%) as a yellow solid; mp 45-46 C; 1H NMR (300 MHz, CDCl3): delta = 2.63 (t, J = 7.2 Hz, 2H), 2.81 (t, J = 7.2 Hz, 2H), 5.69 (s, 1H), 5.94 (s,1H), 7.43 (m, 2H), 7.54 (m, 1H), 7.72 (d, J = 6.9 Hz, 2H), 11.39 (bs, 1H); 13C NMR (75 MHz, CDCl3): delta = 27.2, 32.6, 127.2, 128.2, 129.4, 132.3, 137.5, 145.9, 179.0, 197.8. 108-55-4, As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

Reference£º
Article; Sivak, Ivan; Berke?, Du?an; Ko?i?ek, Jozef; Kolarovi?, Andrej; Tetrahedron Letters; vol. 57; 10; (2016); p. 1079 – 1082;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 108-55-4

The synthetic route of 108-55-4 has been constantly updated, and we look forward to future research findings.

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

108-55-4, In a milliliter three-necked flask, 200 ml of fluorobenzene was added, Then aluminum trichloride (59.4 g, 0.45 mol) was added,And cooled to 15 C with an ice bath, Then, the solution of glutaric anhydride (30 g, 0.3 mol) in fluorobenzene (100 ml) was added dropwise at 15 C, After completion of the dropwise reaction at 30 C for 5 hours,Cold to about 0 deg C, Dropping 200 ml of 1 M hydrochloric acid, Note that the temperature during the dropwise process does not exceed 20 C. After completion of the dropwise addition, the reaction solution was added to a large amount of ice water, Precipitation of solids, filter, Wash the filter cake with steamed water, The filter cake was then added to 800 ml of saturated sodium bicarbonate solution and stirred at room temperature for 1 h, filter, The filtrate was added with activated carbon decolorization. Concentrated hydrochloric acid to adjust the PH value to 1, Solid precipitation, Filter and wash the filter cake with water, After drying, 51.7 g of white solid compound I, Yield 82%.

The synthetic route of 108-55-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Suzhou Puluoda Biological Science and Technology Co., Ltd.; Luo, Ruixue; (14 pag.)CN106397292; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 108-55-4

The synthetic route of 108-55-4 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108-55-4,Dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

A flask was charged with AlCl3 (77.17 mmol, 10.29 g, 2.15 equiv) and dry CH2Cl2 (25 ml) under calcium chloride guard tube and the formed suspension was stirred on ice bath. Subsequently, a solution of glutaric anhydride 10 (35.8 mmol, 4.08 g) in dry CH2Cl2 (12 ml) was added dropwise (t < 8 C). The resulting mixture was stirred on ice bath for 30 minutes and fluorobenzene 11c (35.1 mmol, 3.37 g, 1.0 equiv) was carefully added afterwards. The cooling bath was removed and the mixture was stirred at room temperature for 19 hours, then it was carefully quenched with ice water (20 ml), conc. H2SO4 (10 ml) and again with ice water (60 ml), the aqueous layer was extracted with ethyl acetate (1 x 200 ml, 1 x 100 ml, 1 x 70 ml), the combined organics were washed with half-saturated brine (200 ml), dried over Na2SO4, filtered and concentrated. The crude product was crystallized from ethyl acetate to provide 5-(4-fluorophenyl)-5-oxopentanoic acid (3.80 g, 51%) as a yellow-brown powder;3 mp 141-142 C; 1H NMR (300 MHz, CDCl3): delta = 2.08 (m, 2H), 2.51 (t, J = 7.2 Hz, 2H), 3.05 (t, J = 7.2 Hz, 2H), 7.13 (m, 2H), 7.99 (m, 2H). 5-(4-Fluorophenyl)-5-oxopentanoic acid (16.7 mmol, 3.50 g), paraformaldehyde (50.0 mmol, 1.50 g, 3.0 equiv) and piperidine (0.32 ml, 0.2 equiv) were dissolved/suspended in pyridine (15 ml) and stirred at 70 C for 21 hours. Afterwards, the mixture was poured into 1M H2SO4 (340 ml), the aqueous layer was extracted with ethyl acetate (4 x 100 ml), the combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (EA/hexanes = 1/1 + 0.5% AcOH). The obtained product was repeatedly coevaporated with toluene (4 x 25 ml) under reduced pressure to remove the residual AcOH, yielding 4-(4-fluorobenzoyl)pent-4-enoic acid 9c (3.33 g, 90%) as an orange solid; mp 81-82 C; 1H NMR (300 MHz, CDCl3): delta = 2.62 (t, J = 7.2 Hz, 2H), 2.80 (t, J = 7.2 Hz, 2H), 5.65 (s, 1H), 5.92 (s, 1H), 7.12 (dd, J = 8.7, 8.7 Hz, 2H), 7.78 (dd, J = 5.7, 8.7 Hz, 2H), 10.74 (bs, 1H); 13C NMR (75 MHz, CDCl3): delta = 27.3, 32.5, 115.3 (d, JCF = 21.8 Hz), 126.7, 132.0 (d, JCF = 9.0 Hz), 133.7, 145.9, 165.3 (d, JCF = 252.5 Hz), 178.9, 196.2, 108-55-4

The synthetic route of 108-55-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Sivak, Ivan; Berke?, Du?an; Ko?i?ek, Jozef; Kolarovi?, Andrej; Tetrahedron Letters; vol. 57; 10; (2016); p. 1079 – 1082;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 108-55-4

108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108-55-4,Dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Intermediate 1: 5-(Benzyloxy)-5-oxopentanoic AcidDissolve glutaric anhydride (8.76¡Á10-2 mol) in dichloromethane (300 ml) and place under stirring. Add 4-dimethylaminopyridine (7.88¡Á10-2 mol) and benzyl alcohol (7.88¡Á10-2 mol) and then leave the reaction mixture at ambient temperature. After 4 hours and 30 minutes, the mixture is hydrolysed with aqueous 5% sodium carbonate solution (200 ml). Separate the two phases by decanting. The aqueous phase is then acidified with aqueous 1M hydrochloric acid solution and subsequently extracted with ethyl acetate. The organic phase is washed with brine, dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure.The title product is obtained in the form of a white solid which is used without subsequent purification., 108-55-4

108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LES LABORATOIRES SERVIER; US2010/286225; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 108-55-4

108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Curcumin 8 (100 mg, 0.27 mmol) and glutaric anhydride (31 mg, 0.27 mmol) were dissolved in toluene (15 ml). DMAP (39 mg, 0.32 mmol) was added followed by TEA (150 L, 1 mmol). The reaction mixture was stirred refluxed under inert gas for 6 h. The solvent was evaporated under vacuum. The orange precipitate was re-dissolved in ethyl acetate (50 mL) and washed with 1M HCl (5 mL). The organic phase was extracted, and the solvent was removed and dried. The crude product was purified via column chromatography using CH2Cl2:CH3OH (95:5 (v/v) as eluent. MS (ESI) [C26H26O9]: Calcd: 482.4792 Found: 483.2623 [M + H]+ and 505.2484 [M + Na]+. 1HNMR (CDCl3, 400 MHz, delta ppm): 2.08-2.11 (m, 2H), 2.55 (t, J =11.1Hz, 2H), 2.69 (t, J = 10.8, 2H), 3.86 (s, 3H), 3.93 (s, 3H), 5.81 (s, 2H), 6.44-6.55 (m, 3H), 6.91 (d, 1H), 7.09-7.61 (m, 7H). 13C NMR (CDCl3, 100 MHz, delta ppm): 19.99, 32.22, 32.74, 55.88, 101.42, 101.96, 109.72, 111.52, 114.91, 120.91, 122.24, 123.28, 124.27, 127.00, 134.15, 139.39, 140.96, 141.18, 146.65, 148.54, 151.60, 170.84, 175.56, 181.79, 184.64., 108-55-4

108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Darwish, Shaban; Mozaffari, Saghar; Parang, Keykavous; Tiwari, Rakesh; Tetrahedron Letters; vol. 58; 49; (2017); p. 4617 – 4622;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 108-55-4

108-55-4, 108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A flask was charged with AlCl3 (78.8 mmol, 10.5 g, 2.3 equiv) and dry CH2Cl2 (25 ml) under calcium chloride guard tube and the formed suspension was stirred on ice bath. Subsequently, a solution of glutaric anhydride 10 (34.3 mmol, 3.91 g) in dry CH2Cl2 (15 ml) was added dropwise (t < 7 C). The resulting mixture was stirred on ice bath for 30 minutes and bromobenzene 11b (34.3 mmol, 5.39 g, 1.0 equiv) was carefully added afterwards. The cooling bath was removed and the mixture was stirred at room temperature for 19 hours, then it was poured into ice water (15 ml), acidified with conc. H2SO4 (10 ml), the aqueous layer was extracted with ethyl acetate (1 x 100 ml, 2 x 50 ml), the combined organics were dried over Na2SO4, filtered and concentrated. The crude product was dissolved in ethyl acetate and the resulting solution was added dropwise to a vigorously stirred cold hexanes (1 L). The precipitate was filtered off and dried to provide 5-(4-bromophenyl)-5-oxopentanoic acid (7.93 g, 85%) as a yellow powder;2 mp 125-127 C; 1H NMR (300 MHz, CDCl3): delta = 2.07 (m, 2H), 2.50 (t, J = 7.2 Hz, 2H), 3.04 (t, J = 7.2 Hz, 2H), 7.60 (m, 2H), 7.82 (m, 2H). 5-(4-Bromophenyl)-5-oxopentanoic acid (25.0 mmol, 6.78 g), paraformaldehyde (86.3 mmol, 2.59 g, 3.4 equiv) and piperidine (0.57 ml, 0.24 equiv) were dissolved/suspended in pyridine (42 ml) and stirred at 70 C for 21 hours. Afterwards, the mixture was poured into 1M H2SO4 (200 ml)/conc. H2SO4 (15 ml), the aqueous layer was extracted with ethyl acetate (1 x 150 ml, 2 x 100 ml), the combined organics were washed with half-saturated brine (300 ml), dried over Na2SO4, filtered and concentrated. The crude product was crystallized from ethyl acetate to yield 4-(4-bromobenzoyl)pent-4-enoic acid 9b (3.93 g, 56%) as an orange-yellow solid; mp 127-128 C; 1H NMR (300 MHz, CDCl3): delta = 2.63 (t, J = 6.9 Hz, 2H), 2.80 (t, J = 6.9 Hz, 2H), 5.67 (s, 1H), 5.95 (s, 1H), 7.60 (m, 4H); 13C NMR (75 MHz, CDCl3): delta = 27.2, 32.6, 127.3, 127.4, 131.0, 131.6, 136.3, 145.8, 178.9, 196.6. 108-55-4, 108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Sivak, Ivan; Berke?, Du?an; Ko?i?ek, Jozef; Kolarovi?, Andrej; Tetrahedron Letters; vol. 57; 10; (2016); p. 1079 – 1082;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 108-55-4

108-55-4, As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (2.01 g, 5.46 mmol) of curcumin, and (112 mg, 0.92 mmol) of DMAP in 100 mL THF was added (1.33 mL, 9.55 mmol) of Et3N. (0.685 g, 6 mmol)glutaric anhydride (95%) in 5 mL THF was added slowly dropwise to the curcumin solution. The mixture was stirred and refluxed under argon overnight. THF was removed under vacuum, 55 mL EtOAc was added, followed by the addition of 15 mL1M HC1, the mixture was stirred for 10 minutes. The organic phase was separated and extracted with EtOAc three times; the solvent was removed and dried. The product was purified via column chromatography, eluting with CH2C12: MeOH, 95: 5. Yield:69 %. 1HNMR (CDC13, 400 MHz): oe 7.65 (d, J= 16Hz, 2H), 7.20-6.95 (m, 5H), 6.96 (d, 1H), 6.48-6.57 (m, 2H), 5.85 (s, 2H), 3.98 (s, 3H), 3.90 (s, 3H), 2.75-2.7 1 (t, J= 8 Hz, 2H), 2.61-2.57 (t, J= 8 Hz, 2H), 2.15-2.12 (t, J= 8 Hz, 2H). 13C NMR (CDC13, 100 MHz): oe 184.56, 181.80, 178.26, 170.84, 151.28, 148.03, 146.84, 141.09, 139.40,134.12, 127.53, 124.25, 123.07, 121.73, 120.99, 114.89, 111.37, 109.69, 101.58,55.96, 32.82, 19.92. LC-MS: 483 [M+Hj (figure 1).

108-55-4, As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

Reference£º
Patent; DONG SUNG PHARM. CO., LTD.; JALDE, Shivakumar S; KIM, Yong Wan; SON, Kwang Hee; LEE, Hwan Suk; (53 pag.)WO2018/236193; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 108-55-4

108-55-4, As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Charge 250 g of anhydrous AlCl3 (1.87 moles) to a 2 L 3-neck round bottom flask, add 300 mL fluorobenzene (307.5 g; 3.2 moles) and cool the mixture in an ice bath to 5C. Add a hazy suspension of 100 g glutaric anhydride (0.86 mole) in 400 mL fluorobenzene (4.3 moles) through an addition funnel over a period of 45 min., and maintain the temperature below 12C. Warm the reaction mixture to ambient temperature gradually and agitate at r.t. for about 90 min.; check for completion by NMR. Cool the reaction mixture to 0 to 5C, then add a cold aqueous solution (700 mL) of 1 N HCl carefully to the mixture to destroy any unreacted AlCl3, keeping the temperature of the mixture below 20C during the early part of the acid addition, and below 40C for the rest of the time. Pour the entire mixture into a 2 L 1:1 mixture of water and ice (v/w) to precipitate out crude products, filter the white suspension and wash well with water. Add the white residue to 3 L of aqueous saturated solution (~5%) of NaHCO3, heat the basic mixture on a steam bath for one hour and filter the batch while hot through a thin pad of celite. Cool the filtrate to r.t., add about 320 mL of concentrated HCl dropwise into the filtrate to pH 1 to crystallize out products, and agitate the white suspension in an ice bath for 30 min. Filter the batch, wash the wet cake with ice cold water and dry in a vacuum oven at 50C for 16 h to obtain 143.2 g of 4-(4-fluorobenzoyl)-butyric acid; m.p. 141 to 142C, isolated yield: 79.3%.

108-55-4, As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

Reference£º
Patent; SCHERING CORPORATION; EP1137634; (2005); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Analyzing the synthesis route of 108-55-4

108-55-4, As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108-55-4,Dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Into a 3L three-necked RB flask was charged ethylene dichloride [(500ML),] aluminum chloride [(250GR)] and fluorobenzene [(45GR)] under nitrogen atmosphere. The reaction mixture was cooled to [10C] and a solution of glutaric anhydride [(LOOGR),] fluorobenzene (45gr) and ethylene dichloride [(500ML)] was added slowly over a period of 3hrs between [10-15C.] After maintaining for one hour at [15-18C] the reaction mixture was slowly poured onto a mixture of crushed ice (700gr) and conc. HCI [(300ML)] below [10C.] The reaction mass temperature was raised to reach [25C] and distilled off ethylene dichloride from the reaction mixture below [100C.] After cooling the reaction mixture to [20C,] crude solid was filtered off and washed with [500ML] of water. The wet cake-thus obtained was suspended in 300ml of ethylene dichloride and filtered. The solid compound was dissolved in [600ML] of 4% sodium hydroxide, treated with [15GR] of activated charcoal and filtered. The filtrate was acidified to pH 1. [5-2.] 0 with conc. [HCI] and the precipitated acid was filtered. After washing the wet cake with [500ML] of water, it was dried at [60-70C] to get 130gr of white solid, rn. p. [140-142C.] This solid was dissolved in [500ML] of acetone. The acetone solution was slowly cooled to [15-20C] and the solid filtered, washed with chilled acetone [(50ML)] and dried at [50-70C] to get 120gr of white crystalline solid, m. p. [143C.] Purity by [HPLC] is 99.65%. Desfluoro impurity is less than 0. [05%.]

108-55-4, As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

Reference£º
Patent; Natco Pharma Limited; Venkaian Chowdary Nannapaneni; WO2003/104180; (2003); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics