1-(3-Fluorophenyl)cyclohexanecarboxylic acid → (1-(3-Fluorophenyl)cyclohexyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-fluorophenyl)cyclohexanecarboxylic acid (0.8 g, 3.60 mmol) in THF (10 mL) at 0° C. was added 2M lithium aluminum hydride (2.500 mL, 5.0 mmol) in THF dropwise and the mixture was stirred at 0° C. for 1.5 hrs. The reaction was quenched with Na2SO4.10H2O and stirred for 0.5 hrs. The reaction mixture was filtered through Celite and washed with EtOAc. The filtrate was washed with 1N HCl followed by 1N NaOH and brine. The EtOAc layer was dried over Na2SO4 and evaporated to give (1-(3-fluorophenyl)cyclohexyl)methanol (675 mg, 3.24 mmol, 90% yield) as an oil. 1H NMR (400 MHz, CCl3D) δ ppm 7.33 (1H, td, J=8.02, 6.37 Hz), 7.16 (1H, d, J=7.91 Hz), 7.09 (1H, dt, J=11.26, 2.17 Hz), 6.89-6.96 (1H, m), 3.50 (2H, s), 2.10 (2H, dd, J=12.85, 3.84 Hz), 1.30-1.66 (9H, m).

Provenance & Evidence