Diisopropylethylamine → 3-Benzyloxy-4-methoxy-2-methylpyridine

Participants

Reaction Steps

3-Benzyloxy-2-methyl-4-pyridone (21.5 g, 0.10 mol) was suspended in methanol-acetonitrile (1:9 v/v, 400 ml). Diisopropylethylamine (18.1 g, 0.14 mol) was added to the suspension. The mixture was then stirred. A 2.0 M solution (70 ml) of tetramethylsilyldiazomethane in n-hexane was added dropwise to the mixture, and a reaction was allowed to proceed at room temperature overnight. The reaction solution was concentrated under the reduced pressure. The concentrate was applied to column chromatography on silica gel (Wako Gel C-200, n-hexane-ethyl acetate) to give 17.3 g (yield 76%) of 3-benzyloxy-4-methoxy-2-methylpyridine.

Provenance & Evidence