p-Toluenesulfonic acid → Methyl(2-heptafluoropropylbenzoxazol-5-yl)acetate

Participants

Reaction Steps

A mixture of methyl(3-heptafluorobutyramido-4-hydroxyphenyl)acetate (20.0 g, 0.053 mol) and para-toluenesulfonic acid (1.71 g) in toluene (150 ml) was heated at reflux (a Dean & Stark™ assembly was fitted to remove water) for 24 hours. The mixture was cooled to room temperature and the mixture was diluted with ethyl acetate (150 ml). The mixture was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel, eluting with dichloromethane to give methyl(2-heptafluoropropylbenzoxazol-5-yl)acetate (12.9 g) as an off-white solid.

Provenance & Evidence