Hydrochloric Acid → 1-(Trifluoromethyl)cyclopropanemethanol

Participants

Reaction Steps

Treat a 0° C. solution of 1-(trifluoromethyl)cyclopropanecarboxylic acid (9 g, 58.4 mmol) in ether (140 mL), under N2, portion-wise with LAH (2.9 g, 76 mmol), allow to warm to RT and stir overnight. Re-cool to 0° C., slowly add HCl, warm to RT and separate the layers. Extract the aqueous layer with ether (2×), wash the combined organics with brine, dry over Na2SO4 and concentrate under reduced pressure (water bath temp<30° C.) to afford the title compound (7 g, 86%). 1HNMR (400 MHz, DMSO-d6): δ 4.94 (t, J=6.0 Hz, 1H), 3.54 (d, J=6.0 Hz, 2H), 0.87-0.84 (m, 2H), 0.81-0.79 (m, 2H).

Provenance & Evidence