Dimethylformamide → 3-Benzofurancarboxylic acid, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a DMF (8.0 mL) solution of 1-benzofuran-3-yl trifluoromethanesulfonic acid (1.00 g, 3.76 mmol), 1,1′-diphenylphosphinoferrocene (128 mg, 231 μmol) and palladium acetate (26.0 mg, 116 μmol), methanol (3.5 mL) and triethylamine (1.05 mL, 7.53 mmol) were added thereto at room temperature. Carbon monoxide gas was bubbled for 20 minutes, and then under a carbon monoxide atmosphere, the mixture was heated and stirred at 60° C. for 3 hours. Water (50 mL) was added, and then the mixture was extracted with ethyl acetate (2×30 mL). The organic layer was combined, washed with 1N-hydrochloric acid (30 mL), and then dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure. The obtained residue was purified using silica gel flash column chromatography (Biotage AB: column No. 40M, hexane:diethyl ether=95:5), to obtain the title compound (570 mg, 3.24 mmol, 86%) as a transparent oily matter.

Provenance & Evidence