Ethyl Acrylate → (E)-ethyl 1-(3-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl)cyclopropanecarboxylate

Participants

Reaction Steps

Ethyl 1-(3-bromophenyl)cyclopropanecarboxylate (740 mg, 2.75 mmol) was dissolved in acetonitrile (20 mL) and the solution was treated with ethyl acrylate (3.90 mL, 35.7 mmol) and tri-o-tolyl phosphine (83.7 mg, 0.275 mmol). The reaction mixture was stirred at room temperature until all of the tri-o-tolyl phosphine had dissolved. Palladium acetate (30.9 mg, 0.137 mmol) was added in a single portion and the reaction mixture was stirred at reflux for 16 hr. Palladium acetate was added (10 mg) and the reaction mixture was stirred for another 4 h. The solvent was removed under reduced pressure and the crude material was purified via flash chromatography (pentane/ethyl acetate 95/5 to 92/8) to afford (E)-ethyl 1-(3-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl)cyclopropanecarboxylate (438 mg, 55%). 1H NMR (400 MHz, CDCl3) δ 1.09-1.19 (m, 5H), 1.31 (t, 3H), 1.56-1.63 (m, 2H), 4.03-4.11 (m, 2H), 4.23 (q, 2H), 6.40 (d, 1H), 7.20-7.36 (m, 2H), 7.36-7.42 (m, 1H), 7.44-7.51 (m, 1H), 7.66 (d, 1H).

Provenance & Evidence