General procedure for the synthesis of 4,4-difluorocyclohexanol from 4,4-difluorocyclohexanone: Sodium borohydride (460 mg, 12.17 mmol) was added to a cold solution of 4,4-difluorocyclohexanone (907 mg, 6.76 mmol) in methanol (22 mL) under the conditions of an ice water bath. The reaction mixture was stirred for 5 minutes and then allowed to warm slowly to room temperature and continued stirring for 1 hour. Upon completion of the reaction, the reaction was quenched with water (11 mL) and stirred for 30 minutes. Subsequently, the solvent was removed by concentration on a rotary evaporator and the residue was partitioned between water (11 mL) and dichloromethane (10 mL). The aqueous layer was separated and extracted with dichloromethane (3 x 10 mL). All organic layers were combined, dried with anhydrous magnesium sulfate, filtered and the solvent was concentrated to give the target product 4,4-difluorocyclohexanol (839 mg, 91% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 4.03-3.82 (m, 1H), 2.26-1.98 (m, 2H), 1.98-1.64 (m, 6H), 1.43 (d, J = 3.6 Hz, 1H).
