1197-66-6 2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one 11829691, 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.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.,1197-66-6
(b) Ethyl 2-cyano-2-(2,2,6,6-tetramethyloxan-4-ylidene)acetate (C6) A mixture of 2,2,6,6-tetramethyloxan-4-one (C4)(4.683 g, 0.030 mol), ammonium acetate (0.231 g, 0.003 mol) and ethyl cyanoacetate (C5)(Aldrich, CAS: 105-56-6, CAT: E18425), (5.0865 g, 0.045 mmol) was heated under reflux in toluene (150 mL) for 3 days using a Dean-Stark trap. Analytical TLC indicated a new UV active compound and some starting material plus other impurities (visualised by UV and PMA stain). The reaction was allowed to cool to room temperature, the solvent evaporated, and the pale yellow oil subjected to purification (silica, 80 g, ethyl acetate/hexane; 10/90, 13 x 100 mm tubes). Fractions 15-17 were the most pure by analytical TLC (UV active and stains with PMA; starting material runs slightly lower is not UV active and stains very strongly with PMA) and collected to give the required product as a light yellow crystalline solid (1.9300 g). Fractions 9-14 (1.5249 g) and fractions 18-45 (2.6121 g) were collected separately and re-purified. Fractions 9-14 were purified using chromatography (silica, 25 g, 5/95 ethyl acetate/hexane, 13 x 100 mm tubes) to give the product as colourless crystals (1.2737 g). Fractions 18-45 were purified using chromatography (silica, 40 g, 5/95 ethyl acetate/hexane, 13 x 100 mm tubes) to give the product as a colourless, sweet smelling oil that crystallized on standing (2.6008 g). Total yield of the alkylidene: (5.8045 g, 77%). H NMR (500 MHz, CDCIs) delta 4.27 (q, 2H, J = 7.2 Hz, CH2CH3), 3.04 (s, 2H, 2 x CH), 2.66 (s, 2H, 2 x CH), 1.33 (t, 3H, J = 7.2 Hz, CH3CH2), 1.24 (s, 6H, 2 x CH3), 1.19 (s, 6H, 2 x CH3). 3C NMR (125 MHz, CDCI3) delta 173.68, 161.54, 115.18, 104.97, 75.61 , 75.58, 61.85, 47.22, 42.51 , 30.69, 30.51 , 14.07.
1197-66-6 2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one 11829691, aTetrahydropyrans compound, is more and more widely used in various fields.
Reference£º
Patent; CANCER THERAPEUTICS CRC PTY LTD; STEVENSON, Graeme Irvine; GARAVELAS, Agatha; COSGROVE, Kelly Leanne; REYNOLDS, Kristie Anne; FRANKEN, Nicole Cecilia; WHITTELL, Louise Renee; WIJESEKERA, Hasanthi Punyama; WO2014/41349; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics