Triethylamine → HCID 20728730, compound

Participants

Reaction Steps

A mixture of 2-methoxycarbonylmethyl-6-trifluoromethanesulfonyloxy-benzoic acid methyl ester (2.705 g, 7.6 mmol), LiCl (2.355 g, 55.6 mmol), NEt3 (1.5 mL, 10.8 mmol), Pd[P(C6H5)3]4 (1.09 g, 0.94 mmol), and tributyl (vinyl)tin (2.85 mL, 9.75 mmol) in dioxane (50 mL) was heated at reflux. After 3 h, the reaction was allowed to cool to rt, filtered through a pad of silica gel and concentrated. The crude product was purified by flash chromatography on SiO2 (13% EtOAc/hexanes) to afford 2-methoxycarbonylmethyl-6-vinyl-benzoic acid methyl ester as a yellow solid (1.50 g, 84%): 1H NMR (CDCl3) δ 3.67 (s, 3H), 3.89 (s, 5H), 5.32 (d, J=10.9 Hz, 1H), 5.68 (d, J=17.4 Hz, 1H) 6.82 (dd, J=17.4, 10.9 Hz, 1H), 7.20(d, J=7.1 Hz, 1H), 7.36(m, 1H), 7.50 (d, J=7.8 Hz, 1H).

Provenance & Evidence