Category: 1194-16-7

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2,2-Dimethyltetrahydropyran-4-one 1 (5.0 g, 32.0 mmol) was dissolved in methanol (4.7 ml) and carbon disulfide (4.7 ml, 48.8 mmol) was added in one portion. Malononitrile (2.6 g, 39.0 mmol) was added portionwise and, finally, triethylamine (1.95 ml) was added dropwise. The reaction mixture was stirred at room temperature for 48 h. An orange precipitate was formed, which was filtered (3.90 g), its 1H NMR being consistent with the desired compound 2. From the filtrates, 0.89 g more of 6-amino-3,3-dimethyl-8-thioxo-4,8-dihydro-1H,3H-thiopyrano[3,4-c]pyran-5-carbonitrile were isolated by flash chromatography, eluting first with CH2Cl2 and next with the mixture of solvents CH2Cl2:MeOH 98:2. Yield = 48%. 1H NMR (200 MHz, CDCl3) delta ppm 1.30 (s, 6 H), 2.62 (s, 2 H), 4.66 (s, 2 H), 7.91 (s, 2 H)., 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Taltavull, Joan; Serrat, Jordi; Grcia, Jordi; Gavald, Amadeu; Cordoba, Mnica; Calama, Elena; Montero, Jose Luis; Andres, Miriam; Miralpeix, Montserrat; Vilella, Dolors; Hernandez, Begona; Beleta, Jorge; Ryder, Hamish; Pags, Lluis; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 4946 – 4956;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

To a 500 mL round-bottom flask was added 2,2-dimethyloxan-4-one 329a (10 g,78.02 mmol, 1.00 equiv.) and methanol (100 mL). NaBH4 (5.9 g, 155.96 mmol, 2.00 equiv.)5 was added in several batches at 0C. The resulting mixture vas stirred at room temperaturefor 3 h, then diluted with 200 mL of EA, vvashed vvith brine (l 00 mL x 2), dried overanhydrous sodium sulfate, and concentrated under vacuum The residue vvas purified by silicagel column chromatography eluting with ethyl acetate in petroleum ether (0% tolOO%) togive 2,2-dirnethyloxan-4-ol 329b (9 g, 89%) as a light yellow oil., 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 5: 2,2-dimethyl-4-(4-methylphenyl)oxan-4-ol n-BuLi (26.3 ml, 1.6 M in hexane, 42 mmol) was added dropwise to a solution of 4-bromo-toluene (7.70 g, 45 mmol) in THF (100 ml) at -78 C. under N2. The resulting mixture was stirred at -78 C. for 30 min and a solution of tetrahydro-2,2-dimethyl-4H-pyran-4-one (3.84 g, 30 mmol) in THF (20 ml) was added. The resulting mixture was stirred at -78 C. for another 20 min and quenched by adding MeOH (10 ml). The reaction was concentrated under vacuum and the resulting residue was diluted with EtOAc (500 ml) and washed with sat. NH4Cl (250 ml), brine (250 ml), dried and concentrated to give 2,2-dimethyl-4-(4-methylphenyl)oxan-4-ol as a white solid, which was used without further purification (5.41 g, 82%). 1H NMR (400 MHz, CDCl3) delta 7.36-7.26 (m, 2H), 7.11 (d, J=8.0, 2H), 4.10 (td, J=12.0, 2.2, 1H), 3.71 (ddd, J=11.8, 5.0, 2.1, 1H), 2.28 (s, 3H), 2.11 (ddd, J=13.7, 12.2, 5.0, 1H), 1.72 (dt, J=14.2, 8.3, 2H), 1.58 (dq, J=13.8, 2.2, 1H), 1.44 (s, 3H), 1.38 (s, 1H), 1.14 (s, 3H)., 1194-16-7

As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Patent; Trevena, Inc.; US2012/245181; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

tert-Butyl-2-amino-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate Following a previously reported procedure,42 a mixture of 2,2-dimethyldihydro-2H-pyran-4(3H)-one (0.30 g, 2.34 mmol, 1 eq), tert-butyl cyanoacetate (0.37 mL, 2.57 mmol, 1.1 eq), sulfur (0.083 g, 2.57 mmol, 1.1 eq), morpholine (0.30 mL, 3.51 mmol, 1.5 eq), and ethanol (7 mL) was heated at 50 C. for 16 h. The reaction mixture was then filtered, and the filter cake washed with ethyl acetate (20 mL). Purification by silica gel chromatography (0-20% EtOAc/Hex ramp over 20 min) afforded the desired product tert-butyl 2-amino-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate as a yellow solid (0.63 g, 2.23 mmol, 95% yield). 1H NMR (400 MHz, CDCl3) delta 5.88 (s, 2H), 4.52 (apparent t, J=1.9, 2H), 2.64 (apparent t, J=1.9, 2H), 1.53 (s, 9H), 1.26 (s, 6H). 13C NMR (101 MHz, CDCl3) delta 165.22, 161.77, 130.07, 113.43, 106.94, 80.38, 70.83, 59.81, 38.72, 28.56, 26.46., 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; STC.UNM; University of Kansas; Wandinger-Ness, Angela; Sklar, Larry; Agola, Jacob; Surviladze, Zurab; Aube, Jeffrey; Golden, Jennifer; Schroeder, Chad E.; Simpson, Denise S.; US8765803; (2014); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

To a solution of cap 5b (1.163 g, 3.52 mmol) in dry DCM (20 mL) was added DBU (0.534 g, 3.52 mmol) dropwise at 0C. Then a solution of cap 5a (1.8 g, 14.08 mmol) in dry DCM (20 mL) was added dropwise at 0C. The reaction mixture was allowed to stir at 25C for 3 days. After removal of the solvent, the residue obtained was purified using Si02 chromatography (eluting with petroleum ether/ ethyl acetate = 5:1 to 3: 1) to provide cap 5c as a white solid (0.15 g, 13% yield). 1H NMR (CDCls): delta 7.30-7.35 (m, 5 H), 5.11 (s, 2 H), 3.82-3.88 (m, 3 H), 3.09-3.16 (m, 2 H), 1.84 (s, 2 H), 1.48 (s, 2 H).

1194-16-7, 1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; TONG, Ling; YU, Wensheng; KOZLOWSKI, Joseph A.; CHEN, Lei; SELYUTIN, Oleg; KIM, Seong Heon; DWYER, Michael; HU, Bin; ZHONG, Bin; WAI, Dahai; HAO, Jinglai; SHEN, Changmao; LEI, Zhixin; WANG, Weijun; WO2014/110706; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

LDA (2.75 mL, 20.29 mmol) was added to a stirred solution of 2,2-dimethyldihydro-2H- pyran-4(3H)-one (2.0 g, 15.60 mmol) in Tetrahydrofuran (THF) (40 mL) at -78 C and stirred for 20 mins. 1, 1, 1-trifluoro-N-phenyl-N-((trifluoromethyl)sulfonyl)methanesulfonamide (3.98 mL, 18.73 mmol) was added at -78 C and stirred at 28 C for 19 hr. Reaction mixture was quenched with saturated sodium bicarbonate solution, diluted with water (10 mL), extracted with ether (2X30 mL), washed with brine solution (20 mL). Organic layer was separated, dried over Na2S04, filtered and concentrated to get crude product. Crude product was purified by column chromatography using (100-200) silica gel column chromatography and was eluted with 15% EtOAc in Hexane (gradient system) to afford the desired product 2,2-dimethyl-3,6-dihydro-2H- pyran-4-yl trifluoromethanesulfonate (2.4 g, 5.98 mmol, 38.3 % yield) as a pale yellow liquid GCMS (m/z): 260 [M+H]+., 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2,2-dimethyl tetrehydropyran-4-one (5.0 g, 39.0 mmol) and ethyl diazoacetate (7.1 g, 62.4 mmol) in tetrahydrofuran (100 mL) was added lithium diisopropylamide (2 M in tetrahydrofuran, 35.1 mL, 70.2 mmol) at -78 C under nitrogen. After addition, the reaction mixture was stirred at -78 C for 1H and then quenched by addition of saturated aqueous ammonium chloride (60 mL). The mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 20% ethyl acetate in petroleum ether) to afford ethyl 2-diazo-2-(4-hydroxy-2,2-dimethyl-tetrahydropyran-4-yl)acetate (6.0 g, 63.5% yield) as a yellow oil use as is in the next step.

1194-16-7, As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

To a solution of 2,2-dimethyltetrahydropyran-4-one (10.4 g, 81.14 mmol) in dichloromethane (40 mL) and boron fluoride ethyl ether (11.2 m1,48% ethyl ether) was added (diazomethyl)trimethylSilane (48.0 mL, 96.0 mmol, 2 M in hexane) dropwise at -30 C. After addition, the resulting solution was stirred for 1H at -30 C and then quenched by addition of saturated sodium bicarbonate (30 mL). The resulting mixture was extracted with dichloromethane (3 x 100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 18% ethyl acetate in petroleum ether) to afford a mixture of 7,7-dimethyloxepan-4-one and 2,2-dimethyloxepan-4-one (2.6 g, 22.5% yield, ratiol : 1) as a pale yellow oil., 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: To a solution of 2 , 2-dimethyldlhydro-2if-pyran~4 (3H) -one (1.00 g, 7.80 mmol) in toluene (6 mL) was added lithium bis ftrimethylsilyl) amide (1 M in THF, 8.19 mL, 8.19 mmol) at 0 C. The mixture was stirred for 2 minutes followed by addition of ethyl 2-chloro-2-oxoacetate (1.06 g, 7.80 mmol). The mixture was stirred at 0 C for 5 minutes followed by addition of HOAc (0.64 mL) in H20 (8 mL) . The organic layer was separated, dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was chromatographed over silica gel (0-40% EtOAc in hexanes) to give a yellow oil. The material was dissolved in EtOH (10 mL) . Methylhydrazine (0.103 mg, 2.23 mmol) was added. The solution was heated at 75 C for 1.5 h, cooled to ambient temperature and concentrated. The residue was chromatographed over silica gel (0-40% EtOAc in hexanes) to give ethyl 1 , 6 , 6-trimethyl-l , 4 , 6 , 7- tetrahydropyrano[4, 3-c]pyrazole-3-carboxylate as a thick oil (0.135 g, 38%): NMR (300 MHz, CDClj) 5 4.80 (s, 2H) , 4.32 (q, J = 7.1 Hz, 2H) , 4.14 (s, 3H), 2.63 (s, 2H) , 1.36 (t, J = 7.1 Hz, 3H) , 1.30 (s, 6H) ; MS (ESI+) /z 239 [ +H]*., 1194-16-7

As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; PETRUKHIN, Konstantin; CIOFFI, Christopher; JOHNSON, Graham; DOBRI, Nicoleta; FREEMAN, Emily; CHEN, Ping; CONLON, Michael; ZHU, Lei; WO2014/152013; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 2,2-dimethyltetrahydropyran-4-one 1 (1.3 g, 0.01 mol)[8], furfural (1.0 g, 0.01 mol), ethyl cyanoacetic acid (1.1 g,0.01 mol), and ammonium acetate (6.2 g, 0.08 mol) in 30 mL of absolute ethanol was boiled with stirring for 6 h. After cooling, the crystals were filtered off, washed with water, diethyl ether, dried and recrystallized from ethanol. Yield 1.3 g (49 %), mp 289-290 C. IR spectrum, nu, cm-1: 3300, 3150, 3050 (N-H, C-H), 2240 (C?N), 1650 (C=O). 1H NMR spectrum, delta, ppm: 1.29 s (6H, 2CH3), 2.54 br. s(2H, CH2), 4.55 br. s (2H, OCH2), 6.68 d. d (1H, H4furan,J = 3.6, 1.7 Hz), 7.24 br. d (1H, H3furan, J= 3.6 Hz), 7.80 d.d (1H, H5furan, J = 1.7, 0.6 Hz), 12.46 br. s (1H, NH). 13C NMR spectrum, delta, ppm: 25.8, 37.3, 59.5, 68.8, 103.6, 108.0, 111.8, 115.6, 115.8, 143.7, 144.8, 146.1, 146.4, 159.9. Found, % C 66.59; H 5.31; N 10.32. C15H14N2O3. Calculated, %: C 66.66; H 5.22; N 10.36., 1194-16-7

As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Article; Dabaeva; Baghdasaryan; Paronikyan; Tamazyan; Ayvazyan; Dashyan, Sh. Sh.; Russian Journal of General Chemistry; vol. 89; 12; (2019); p. 2364 – 2368; Zh. Obshch. Khim.; vol. 89; 12; (2019); p. 1842 – 1847,6;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics