Acetic Acid → Ethyl-3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

Participants

Reaction Steps

3-Trifluoromethylaniline (2.50 g, 15.5 mmol) and ethyl acetoacetate (2.32 g, 17.8 mmol) are dissolved in absolute ethanol in a 500 ml round bottom flask equipped with a stir bar and a reflux condenser. Magnesium sulphate monohydrate (2.58 g, 18.6 mmol) and glacial acetic acid (14 mg, 0.23 mmol) are added. The suspension is stirred rigorously at reflux for 16 hours under an argon atmosphere. The crude reaction mixture is cooled to room temperature, filtered and concentrated in vacuo to give an oil. The oil is chromatographed over silica gel with cyclohexane/ethyl acetate mixtures as eluent to yield a pale yellow oil which is analytically pure.

Provenance & Evidence