Methanol → Bmy 42393

Participants

Reaction Steps

A mixture of methyl 2-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetate (2.25 g, 5.5 mmol), 3N sodium hydroxide solution (5.5 mL) and methanol (50 mL) was heated to reflux on a steam bath. After 5 minutes, the mixture was cooled, the methanol evaporated and the residue diluted with water. Warming provided a solution which was diluted with 1N hydrochloric acid solution to pH 3 to give an oily precipitate. The mixture was extracted with CH2Cl2 and the organic extracts washed twice with water and once with saturated sodium chloride solution. Concentration, after drying over sodium sulfate, left a pale yellow solid which was recrystallized twice from a mixture of hexanes and CH2Cl2 (2:1) to give 2-[3-[2-(4,5-diphenyl-2-oxazolyl)-ethyl]phenoxy]acetic acid (1.74 g, 80%), m.p. 153.3°-154.5° C.

Provenance & Evidence