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
To a stirred suspension of zinc powder (0.54 g, 8.13 mmol) in THF (20 mL) was slowly added TIC) 4 (0.45 mL, 4.07 mmol) via syringe at room temperature under a nitrogen atmosphere. The mixture was heated at reflux for 2 h. A solution of (4- bromophenyl) (3-fluoro-4-hydroxyphenyl) methanone (82) (0.30 g, 1.02 mmol) and 2,2, 6, 6-tetramethyl tetrahydro-4H-pyran-4-one (0.49 g, 3.05 mmol) in THF (6 mL) was added to the mixture. The reaction mixture was heated at reflux with stirring under a nitrogen atmosphere for 1.5 h. The reaction mixture was allowed to cool to room temperature. To the reaction mixture was slowly added 10% aqueous K2CO3 (20 mL). The reaction mixture was filtered through a pad of Celite and the pad was washed with EtOAc (100 mL). The filtrate was transferred to a separatory funnel and the layers were separated. The aqueous layer was further extracted with EtOAc (25 mL). The combined organic phase was washed with brine, dried over NA2SO4, filtered, and the filtrate was concentrated to give the crude product as yellow oil. The crude product was purified by chromatography on a silica gel column eluted with a gradient from hexanes to 15% EtOAc: hexanes to give 0.40 g (94%) of compound 136 as a YELLOW FOAM. H NMR (400 MHz, CDCI3) : 8 1.20 (s, 6H), 1.22 (s, 6H), 2.18 (s, 2H), 2.23 (s, 2H), 5.04 (d, J = 4.0 Hz, 1 H), 6.80-6. 88 (m, 2H), 6.93 (t, J = 8.6 Hz, 1 H), 7.02 (d, J = 8.4 Hz, 2H), 7.42 (d, J = 8.3 Hz, 2H). LCMS (ES): m/z 417 (M-H)
The synthetic route of 1197-66-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/12220; (2005); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics