1-(4-Fluorophenyl)cyclohexane-1-carboxylic acid → (1-(4-Fluorophenyl)cyclohexyl)methanol

Participants

Reaction Steps

A 1 M solution of borane-THF complex (16.7 mL, 16.7 mmol) was slowly added to a solution of (1-(4-fluorophenyl)cyclohexane carboxylic acid (928 mg, 4.18 mmol) in THF (15 mL) at room temperature under a nitrogen atmosphere. After 20 min., the reaction mixture was refluxed for 16 hrs, cooled to room temperature and quenched by the dropwise addition of 1N HCl until further addition caused no more gas evolution. Ethyl acetate and 1N sodium hydroxide were added. The organic layer was washed with 1N sodium hydroxide (2×), brine, dried over sodium sulfate, filtered, and evaporated in vacuo to yield the (1-(4-fluorophenyl)cyclohexyl)methanol (950 mg, 100% yield) as a light tan oil containing some solid.

Provenance & Evidence