Diisobutylaluminumhydride → HCID 68785918, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of methyl 6-methoxy-4-trifluoromethylnicotinate (300 mg, 1.35 mmol) in toluene (10 mL) was added diisobutylaluminum hydride (DIBAL, 1 M/toluene, 1.35 mL). The mixture was warmed slowly to room temperature and stirred for 2 days. Additional DIBAL (1 M/toluene, 2 mL) was added to complete the reaction. After stirring for 4 hours, the mixture was quenched with saturated aqueous ammonium chloride solution (1 mL), dried over anhydrous magnesium sulfate, filtered through a pad of celite, and concentrated under reduced pressure to give 6-methoxy-4-trifluoromethyl-3-pyridinemethanol (220 mg, 78.6%). The crude product was used directly in the following Swern oxidation.

Provenance & Evidence