Hydrochloric Acid → (E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propenol

Participants

Reaction Steps

A solution of diisobutyl aluminum hydride in toluene (1.5M, 51 ml) was added dropwise to a solution of ethyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate (14.0 g) in dichloromethane (200 ml) at 0° C. After stirring for 30 minutes, 2N hydrochloric acid (150 ml) was added at 0° C., and the mixture was stirred for 1 hour. The dichloromethane layer was separated, washed with saturated brine and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave crystals of (E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propenol (11.5 g, 92%). The crystals were recrystallized from ethyl acetate. Colorless prisms, mp: 118-119° C.

Provenance & Evidence