Hydrochloric Acid → (1R)-1-[4-(trifluoromethyl)phenyl]ethanol

Participants

Reaction Conditions

Reaction Steps

To (S)-2-methyl-CBS-oxazaborolidine (Callery, 1M in toluene, 1 eq.) at −45° C. was added BH3.Me2S (1.06 eq.). This solution was stirred for 10 minutes at −45° C. and then placed in a −30° C. cooling bath before the slow dropwise addition of a 1M dichloromethane solution of 4′-(trifluoromethyl)acetophenone. The reaction mixture was allowed to stir for 214 3 hours at −30° C. After completion of the reaction, excess MeOH was added followed by 1N HCl. After warming up to room temperature, the resulting mixture was filtered through a pad of celite pad eluted with 30% EtOAc in hexane. The organic and aqueous layers were separated and the organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting oil was purified by flash chromatography (20% EtOAc in hexane) to afford the title compound.

Provenance & Evidence