Methanol → (E)-3-[7-Hydroxy-6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-acrylic acid methyl ester

Participants

Reaction Steps

Mixture of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran (50 mg, 0.10 mmol) and methylacrylate (0.5 mL, excess) in a mixture of acetonitrile: TEA; 1 mL:0.5 mL was degassed with nitrogen and palladium acetate (10 mg) was added to it. Reaction mixture was stirred for one hour under nitrogen at reflux, more palladium acetate (15 mg) was added and the refluxing was continued for 7 hours (monitored by tlc). Methanol (1 mL) was added followed by the addition of potassium carbonate (70 mg, 0.51 mmol) and stirring was continued for 1 hour. Solvent was distilled and the crude material was purified over silica gel column (eluent Hexane:diethylether; 1:1) to afford the title compound as yellow crystalline solid (17 mg, 37%); 1H NMR (300 MHz, CDCl3) δ 7.61(d, 1H, J=15.76 Hz), 7.14(s, 2H, benzoyl Hs), 6.98(d, 1H, J=8.64 Hz), 6.89(d, 1H, J=8.69 Hz), 6.81(d, 1H, J=15.78 Hz), 3.96(s, 3H, OMe), 3.95(s, 3H, OMe), 3.81(s, 6H, 2×OMe), 3.77(bs, 3H, OMe).

Provenance & Evidence