General procedure for the synthesis of (2-trifluoromethyl-pyridin-3-yl)-methanol from ethyl 2-trifluoromethylnicotinate: sodium borohydride (0.35 g, 9.1 mmol) was suspended in anhydrous tetrahydrofuran (20 mL). Anhydrous tetrahydrofuran solution (20 mL) of ethyl 2-trifluoromethylnicotinate (1.00 g, 0.46 mmol) was added dropwise to the stirred suspension under ice bath cooling. The reaction mixture was stirred at 4°C for 16 hours. Upon completion of the reaction, methanol (5 mL) was added to quench the residual sodium borohydride, followed by the addition of 15% aqueous sodium hydroxide solution (25 mL). The resulting mixture was continued to be stirred at 25 °C for 30 min, followed by removal of tetrahydrofuran and methanol by rotary evaporation. The remaining aqueous phase was extracted with ethyl acetate (3 x 25 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated by rotary evaporation to afford the target product (2-trifluoromethyl-pyridin-3-yl)-methanol as a yellow oil (0.61 g, 75% yield), which could be used in subsequent reactions without further purification. The product was characterized by 1H-NMR (CDCl3): δ 8.64 (d, J = 4.5 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H), 7.57 (dd, J = 8.0, 4.5 Hz, 1H), 4.98 (s, 2H), 1.99 (s, 1H). Mass spectrum (ESI+): m/z (M + H)+ = 178.
