Dimethylformamide → [6-(Trifluoromethyl)pyridin-2-yl]methanol

Participants

Reaction Conditions

Reaction Steps

A solution containing 2.00 g of 2-bromo-6-trifluoromethylpyridine dissolved in 50 ml of toluene was cooled to −78° C. followed by dropping in 4.0 ml of n-butyllithium (2.77 mol/L) and stirring for 10 minutes at −78° C. 0.96 g of N,N-dimethylformamide were dropped therein followed by further stirring for 10 minutes at −78° C. following completion of the reaction. 0.67 g of sodium borohydride and 5 ml of methanol were added to the resulting reaction mixture followed by heating to room temperature and stirring for 1 hour at room temperature. Following completion of the reaction, aqueous ammonium chloride solution was added to the reaction liquid followed by extraction with ethyl acetate. The ethyl acetate layer was dried by addition of anhydrous magnesium sulfate followed by filtering and distilling off the solvent from the filtrate under reduced pressure to obtain 1.70 g of a crude product in the form of (6-trifluoromethylpyridin-2-yl) methanol.

Provenance & Evidence