1-(Trifluoromethyl)cyclopropane-1-carboxylic acid → 1-(Trifluoromethyl)cyclopropanemethanol

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(trifluoromethyl)cyclopropane-1-carboxylic acid (3 g, 19.47 mmol) in THF (32.4 mL) was treated with borane-THF complex (1.0 M, 31.2 mL, 31.2 mmol) and heated at 40° C. overnight. The mixture was cooled in an ice bath, carefully quenched with satd. NH4Cl, filtered through diatomaceous earth and rinsed well with EtOAc. The filtrate was extracted with EtOAc (2×) and the combined organics were washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to afford (1-(trifluoromethyl)cyclopropyl)methanol (2.46 g, 90%). 1H NMR (400 MHz, DMSO-d6): δ 4.93 (t, J=6.0 Hz, 1H), 3.52 (d, J=6.0 Hz, 2H), 0.86-0.75 (m, 4H).

Provenance & Evidence