HCID 67158968, compound → HCID 67159110, compound

Participants

Reaction Steps

A solution of (1RS,2RS,4RS)-4-((tert-butyldiphenylsilyloxy)methyl)-2-(4-chloro-3-(trifluoromethyl)phenyl)-2-methylcyclohexanol (1.35 g, 2.406 mmol) in dichloromethane (40 mL) was treated with Celite (1.5 g, 24.97 mmol) and pyridinium chlorochromate (0.778 g, 3.61 mmol). The resulting mixture was stirred at rt for 19.5 h, then diluted with Et2O and stirred vigorously at rt. The resulting slurry was filtered through a pad of Florisil and the solids were rinsed thoroughly with Et2O. The filtrate was concentrated under vacuum, taken up in dichloromethane and concentrated. The resulting residue was purified by column chromatography on silica gel, eluting with 0-15% ethyl acetate-hexane, to provide (2RS,4RS)-4-((tert-butyldiphenylsilyloxy)methyl)-2-(4-chloro-3-(trifluoro-methyl)phenyl)-2-methylcyclohexanone as a colorless gum (1.338 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.66 (m, 4 H), 7.53 (d, J=2.0 Hz, 1 H), 7.43 (m, 7 H), 7.26 (m, 1 H), 3.58 (dd, J=9.8, 5.5 Hz, 1 H), 3.48 (dd, J=9.8, 7.1 Hz, 3 H), 2.79 (dt, J=14.6, 3.0 Hz, 1 H), 2.33 (m, 2 H), 2.07 (m, 1 H), 1.93 (m, 1 H), 1.49 (dd, J=14.6, 12.6 Hz, 1 H), 1.41 (m, J=12.5, 4.9 Hz, 1 H), 1.26 (s, 3 H), 1.09 (s, 9 H).

Provenance & Evidence