Imidazole → HCID 67158968, compound

Participants

Reaction Steps

A solution of (1RS,2RS,4RS)-2-(4-chloro-3-(trifluoromethyl)phenyl)-4-(hydroxymethyl)-2-methylcyclohexanol (1.253 g, 3.88 mmol) in DMF (15 mL) was treated with imidazole (0.581 g, 8.54 mmol) followed by tert-butyldiphenylchlorosilane (1.097 mL, 4.27 mmol). The resulting mixture was stirred at rt for 29 h. After this time, the solution was diluted with ethyl acetate (150 mL), washed three times with water, once with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel, eluting with 5-25% ethyl acetate-hexanes, to provide (1RS,2RS,4RS)-4-((tert-butyldiphenylsilyloxy)methyl)-2-(4-chloro-3-(trifluoromethyl)phenyl)-2-methylcyclohexanol as a colorless gummy glass (1.599 g, 73%). 1H NMR (400 MHz, CDCl3) δ 8.14 (s, 1 H), 7.82 (dd, J=8.5, 1.6 Hz, 1 H), 7.63 (t, J=6.6 Hz, 4 H), 7.40 (m, 7 H), 3.72 (dt, J=12.0, 3.5, 3.4 Hz, 1 H), 3.42 (m, 2 H), 2.43 (m, 1 H), 1.69 (m, 5 H), 1.33 (s, 3 H), 1.12 (m, 2 H), 1.06 (s, 9 H).

Provenance & Evidence