Sodium borohydride → HCID 11062593, compound

Participants

Reaction Steps

3,5-Dimethyl-2-methoxycarbonyl-4-pyrone 3 (R=Methyl) (294 mg, 1.62 mmol) and sodium borohydride (154 mg, 4.07 mmol) were dissolved in methanol (10 ml) and the resulting solution stirred at room temperature for 45 minutes. Silica gel (5 ml) was added and the solvent evaporated. The residue was applied to a pre-packed chromatography column assembled from silica gel (45 ml) in dichloromethane: ethyl acetate (1:1, v/v). Elution with firstly dichloromethane: ethyl acetate (1:1, v/v), then ethyl acetate, then methanol: ethyl acetate (1:3, v/v) gave 3,5-dimethyl-2-hydroxymethyl-4-pyrone 4 (230 mg, 92%) as a white solid. 1H-NMR (CDCl3) δ 1.93 (s, 3H), 2.01 (s, 3H), 4.60 (s, 2H), 7.71 (s, 1H); selected IR (cm-1, nujol) 3150-3500 (br, s), 1653 (s); Ms (APCI+) m/z (%) 155 (MH+, 100).

Provenance & Evidence