Acetic Acid → HCID 86653598, compound

Participants

Reaction Steps

A solution of methyl (4RS,6RS)-4-((tert-butyl-diphenylsilyloxy)methyl)-6-(4-chloro-3-(trifluoromethyl)-phenyl)-6-methylcyclohex-1-enecarboxylate (495 mg, 0.823 mmol) in THF (5 mL) was treated at rt with acetic acid (0.118 mL, 2.058 mmol), followed by tetrabutylammonium fluoride (1.0 M in THF, 1.235 mL, 1.235 mmol). The resulting solution was stirred for 17.5 h. After this time, the solution was diluted with ethyl acetate, washed sequentially with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, dried over sodium sulfate and then concentrated under vacuum to yield a residue. The residue was purified by column chromatography on silica gel, eluting with 20-50% ethyl acetate-hexane, to provide methyl (4RS,6RS)-6-(4-chloro-3-(trifluoromethyl)phenyl)-4-(hydroxymethyl)-6-methylcyclohex-1-enecarboxylate as a colorless gum (281 mg, 94%). Mass spectrum m/z 363.0 (M+H+). 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=2.2 Hz, 1 H), 7.39 (d, J=8.6 Hz, 1 H), 7.32 (dd, J=8.6, 2.2 Hz, 17 H), 7.28 (dd, J=5.4, 2.5 Hz, 1 H), 3.64 (s, 3 H), 3.42 (m, 2 H), 2.45 (m, 1 H), 2.00 (m, 1 H), 1.76 (m, 1 H), 1.65 (s, 3 H), 1.53 (m, 2 H), 1.42 (br. s, 1 H).

Provenance & Evidence