Methyl Acrylate → HCID 58907415, compound

Participants

Reaction Steps

A solution of 3-bromophenylacetone (50.0 g, 235 mmol), methyl acrylate (40.4 g, 469 mmol), palladium(II)acetate (7.9 g, 35.2 mmol), tri-ortho-tolylphosphine (21.4 g, 70.4 mmol) and triethylamine (82 mL) in acetonitrile (900 mL) was heated at reflux under a nitrogen atmosphere for 16 hours. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. Purification by flash column chromatography eluting with pentane:ethyl acetate 90:10 to 70:30 gave the title compound as an orange oil (54.3 g). 1H NMR (400 MHz, CD3OD) δ: 2.15 (3H, s), 3.70 (2H, s), 3.77 (3H, s), 6.43–6.39 (1H, d), 7.20–7.18 (1H, d), 7.34–7.31 (2H, t), 7.41–7.39 (1H, d), 7.66–7.62 (1H, d); LRMS ESI: m/z 241 [M+Na]+, 217 [M−H]−.

Provenance & Evidence