Methanol → HCID 19965653, compound

Participants

Reaction Steps

A toluene solution of diisobutylaluminum hydride (1.5 M, 17 ml) was added drop by drop to a suspension of ethyl (E)-4-[2-[5-methyl-2-(2-naphthyl)4-oxazolyl]vinyl]cinnamate (4.20 g) in dichloromethane (100 ml) at 0° C. After the mixture was stirred at room temperature for 4 hours, methanol (2 ml) and then water (6 ml) were added at 0° C. After the insoluble substances were filtered off, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to yield a crystal of (E,E)-3-[4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]vinyl]phenyl]-2-propenol from the fraction eluted with ethyl acetate-chloroform (5:95, v/v), which was then recrystallized from chloroform-ethanol to yield light yellow prisms (3.04 g, 81%) having a melting point of 184°-185° C.

Provenance & Evidence