Ethanol → Ethyl 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoate

Participants

Reaction Steps

A mixture of methyl 4-amino-4-thioxobutanoate (0.3 g, 2.03 mmol) and 2-bromo-4-fluoroacetophenone (0.440 g, 2.03 mmol) in EtOH (10 mL) was refluxed for 3 h. The reaction mixture was cooled to room temperature and solvent was removed under reduced pressure. The organic product was extracted with EtOAc and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 8-10% EtOAc in petroleum ether) to afford ethyl 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoate (0.45 g, crude containing 7% of methyl ester product), which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 7.88-7.83 (m, 2H), 7.28 (s, 1H), 7.13-7.07 (t, J=8.8 Hz, 2H), 4.22-4.15 (q, J=7.0 Hz, 2H), 3.40-3.35 (t, J=7.3 Hz, 2H), 2.93-2.88 (t, J=7.3 Hz, 2H), 1.30-1.25 (t, J=7.1 Hz, 3H). MS (ESI) m/z: Calculated for C14H14FNO2S: 279.07. found: 280.2 (M+H)+.

Provenance & Evidence