General procedure for the synthesis of (2-trifluoromethyl-pyridin-4-yl)-methanol from 2-(trifluoromethyl)isonicotinic acid: 2-(trifluoromethyl)isonicotinic acid (10.0 g, 52.4 mmol) was dissolved in tetrahydrofuran (150 mL) and cooled down to 0 °C. Under nitrogen protection, 1 mol/L borane-tetrahydrofuran solution (105 mL, 105 mmol) was slowly added. The reaction mixture was heated to 75 °C and the reaction was stirred for 2 hours. After completion of the reaction, the mixture was carefully poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford the target product (2-trifluoromethyl-pyridin-4-yl)-methanol (5.60 g, 31.6 mmol, 60% yield). Mass spectrum (ESI) m/z: 178 ([M+H]+). 1H NMR (300 MHz, CDCl3): δ 8.68 (d, J=4.8Hz, 1H), 7.79 (s, 1H), 7.64 (d, J=4.8Hz, 1H), 5.62 (br-s, 1H), 4.66 (s, 2H).
