4-Fluorobenzamide → Ethyl[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetate

Participants

Reaction Steps

A suspension of 4-fluorobenzamide (12.9 g) and ethyl 4-bromo-3-oxopentanoate (Chem Abs No. 36187-69-6; 5.24 g) in anhydrous toluene (120 ml) was heated at 140° C. for 19 h, using a Dean-Stark trap. The solution was allowed to cool, filtered, and the residual solid washed with toluene (30 ml). The combined filtrate and washings were concentrated in vacuo to give a brown oil, which was purified by Biotage flash chromatography on silica gel (90 g column), eluting with ethyl acetate:cyclohexane (5:95, 7.5:92.5, 10:90), to give thetitle compound as a yellow solid (2.98 g).

Provenance & Evidence