Acetic Acid → ethyl (2Z)-3-(methylamino)-3-phenylacrylate

Participants

Reaction Steps

To a solution of methylamine (65.03 mL of a 2M solution in THF, 130.06 mmol) and ethyl benzoylacetate (4.505 mL, 26.01 mmol) in EtOH (26 mL) was added HOAc (7.45 mL, 130.06 mmol). The mixture was then heated to reflux for 15 h. At this time, crude 1H NMR revealed only product and MeNH2—HOAc. The reaction mixture was then cooled to RT, and the solvent was removed in vacuo. The crude reaction was then extracted with 1 N HCl and DCM. The organic layer was then dried over MgSO4, and the solvent was removed in vacuo to yield 5.3 g (99%) of ethyl (2Z)-3-(methylamino)-3-phenylacrylate. The product was used as is in subsequent reactions. 1H NMR (500 MHz, CDCl3) ppm: 8.50 (br s, 1H), 7.40 (m, 3H), 7.35 (m, 2H), 4.59 (s, 1H), 4.15 (q, J=7.0 Hz, 2H), 2.77 (d, J=5.0 Hz, 3H), 2.50 (s, 3H), 1.27 (t, J=7.0 Hz, 3H).

Provenance & Evidence