Isopropenyl acetate → Methyl 5-(propan-2-one-yl)benzofuran-2-carboxylic acid

Participants

Reaction Steps

A solution of methyl 5-bromobenzofuran-2-carboxylic acid (2.4 g, 9.3 mmol), tributyltin methoxide (4.0 mL, 14 mmol), isopropenyl acetate (1.4 mL, 14 mmol), palladium (II) acetate (0.1 g, 0.5 mmol) and tri-o-tolylphosphine (0.3 g, 1mmol) in toluene (6 mL) were heated at 95° C. for 2 hours. The reaction solution was concentrated in vacuo and subjected to flash chromatography on silica gel (25% ethyl acetate:hexanes) to afford the title compound as a colorless solid, (1.8 g; m.p. 77-79° C., Analytical Calculated for C13H12O4 :C, 67.25; H, 5.21. Found: C, 67.12; H, 4.95).

Provenance & Evidence