Methanol → 4-(Hydroxymethyl)pyridin-2(1H)-one

Participants

Reaction Steps

To a stirred solution of methyl 2-oxo-1,2-dihydropyridine-4-carboxylate (300 mg, 1.96 mmol) in THF (20 mL) was added diisobutylaluminium hydride (1.0 M in THF, 20 mL, 20 mmol). The mixture was stirred at RT for 3 h, then MeOH (2 mL) and H2O (1 mL) were added. The mixture was stirred at RT for 20 minutes and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (DCM:MeOH=8:1) to afford 4-(hydroxymethyl)pyridin-2(1H)-one as a white solid (150 mg, 61.2%). MS (ES+) C6H7NO2 requires: 125. found: 126 [M+H]+.

Provenance & Evidence