Vanillin → HCID 21224400, compound

Participants

Reaction Steps

Diethyl azodicarboxylate (DEAD) (4.71 g) was added dropwise, under ice-cooling, to a mixture of 1-(5-methyl-2-phenyl-4-oxazolyl)ethanol (5.0 g), vanilline (3.75 g), triphenylphosphine (Ph3P) (7.1 g) and tetrahydrofuran (THF) (80 ml). The reaction mixture was stirred for 8 hours at room temperature and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:4, v/v), was obtained 3-methoxy-4-[1-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (4.48 g, 54%), which was recrystallized from ethyl acetate-hexane to give colorless needles, m.p.104-105° C.

Provenance & Evidence