Water → 2-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol

Participants

Reaction Steps

2.6 g (8.40 mmol) of the above prepared [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic acid methyl ester dissolved in 15 ml of dry tetrahydrofuran was added under an argon atmosphere within 15 minutes to a stirred suspension of 0.38 g (10 mmol) of lithium aluminum hydride in 5 ml of tetrahydrofuran. The reaction was exothermic. Subsequently, the mixture was stirred at room temperature for 1 hour. Then, 1 ml of ethyl acetate was dropped into the reaction mixture, followed by water, drop after drop, under argon, with stirring and cooling until the gas evolution ceased. The reaction mixture was then diluted with 50 ml of ethyl acetate, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated i. V. and the residue was chromatographed on SiO2 with a mixture of dichloromethane and tert.-butyl methyl ether (4/1 vol./vol.) as eluent. Thereby, 1.88 g of the title compound was obtained as white solid.

Provenance & Evidence