Diethyl Ether → HCID 59225756, compound

Participants

Reaction Steps

To a magnetically stirred solution of methyl Grignard (19.9 mL of a 3 M solution in ether (Et2O), 59.7 mmol) in Et2O (167 mL) was added a solution of 2-trifluoromethylpyrimidine-5-carbaldehyde (9.56 g, 54.3 mmol) in Et2O (50 mL) at 0° C., and the resulting pale yellow solution was warmed to room temperature (RT) and stirred for 2.5 h. The reaction was quenched by the addition of saturated aqueous ammonium chloride (NH4Cl) (50 mL) at 0° C., and the mixture was warmed to RT. The phases were separated and the organic phase was dried over Na2SO4, filtered, and concentrated to give a light yellow oil (9.32 g crude). The oil was purified by flash chromatography (330 g SiO2, 0→100% EtOAc/hexanes gradient) to give 1-(2-trifluoromethylpyrimidin-5-yl)ethanol (E) (8.87 g, 85%) as a light yellow solid: mp 43-45° C.; 1H NMR (300 MHz, CDCl3) δ 8.92 (s, 2H), 5.15-5.07 (m, 1H), 2.26 (d, J=4.0 Hz, 1H), 1.62 (d, J=6.5 Hz, 3H); MS (EI) m/z 192 (M)+.

Provenance & Evidence