(2-Phenyl-2H,4H-[1,3]dioxino[5,4-b]pyridin-6-yl)methanol → 2-Phenyl-2H,4H-[1,3]dioxino[5,4-b]pyridine-6-carbaldehyde

Participants

Reaction Steps

To a suspension of 38.8 g. (0.4 mole) of activated manganese dioxide in 400 ml. of benzene is added 48.6 g. (0.2 mole) of 6-hydroxymethyl-2-phenyl-4H-pyrido[3,2-d]-1,3-dioxin in 250 ml. of the same solvent, and the mixture stirred at the reflux temperature overnight. The mixture is filtered while hot (50° C.) and the filtrate concentrated under vacuum to an oily foam, 49.7 g. The intermediate product is purified by chromatographing on a silica gel column (1 kg. 60-200 mesh silica gel; 8 cm × 75 cm column), the product being eluted with ethyl acetate. The eluates are combined and evaporated to dryness, 11.75 g., m.p. 110°-114° C.

Provenance & Evidence