(4-Trifluoromethyl-pyridin-3-yl)-methanol

175204-82-7

198401-76-2

General procedure for the synthesis of (4-trifluoromethyl-3-pyridine)-methanol from 4-trifluoromethylnicotinic acid methyl ester: 0.37 g (9.7 mmol) of lithium aluminum hydride was dissolved in 100 ml of THF and the solution was cooled down to -50 °C. Subsequently, a solution of 2.0 g (9.8 mmol) of methyl 4-trifluoromethylnicotinate dissolved in 30 ml of THF was added slowly and dropwise. The reaction mixture was stirred continuously at -50 °C for 3 h to ensure complete reaction. Upon completion of the reaction, ethyl acetate was added cautiously and stirred briefly before adding water and continuing to stir. The reaction mixture was separated by vacuum filtration and the filtrate was extracted with ethyl acetate. The organic layer obtained by extraction was washed sequentially with water and aqueous sodium chloride solution and subsequently dried with anhydrous magnesium sulfate. The dried solution was distilled under vacuum to remove the solvent, and the residue was purified by silica gel column chromatography (unfolding agent: hexane-ethyl acetate mixed solvent) to finally obtain 0.6 g (35.3% yield) of (4-trifluoromethylpyridin-3-yl)-methanol as a yellow oil. The product was analyzed by 1H-NMR [CDCl3/TMS, δ (ppm)]: 9.00 (1H, s), 8.73 (1H, d), 7.51 (1H, d), 4.95 (2H, s).