Triethylamine → (5-(Trifluoromethyl)pyridin-3-yl)methanol

Participants

Reaction Steps

To a solution of 5-(trifluoromethyl)nicotinic acid (1.0 g, 5.23 mmol) and triethylamine (0.802 mL, 5.75 mmol) in benzene was added ethyl chloroformate (0.548 mL, 5.75 mmol) and the reaction was stirred 1 hour at room temperature. The reaction was filtered to remove salts and concentrated to dryness. The residue was taken up in tetrahydrofuran and cooled to −78° C. Lithium aluminum hydride (2M in THF, 2.88 mL, 5.75 mmol) was added dropwise and aged 0.5 hour. Reaction was quenched with water and stirred with 0.5N NaOH for 1 hour. The product was extracted with ethyl acetate (2×), washed brine, dried over sodium sulfate and concentrated to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calc'd for C7H6F3NO: 178.04; found: 178.06.

Provenance & Evidence