Hydrochloric Acid → Methyl 6-hydroxybenzofuran-3-carboxylate

Participants

Reaction Steps

To 6-(tert-butyl-dimethyl-silanyloxy)-benzofuran-3-carboxylic acid methyl ester (2.4 g, 7.7 mmol) was added 1% HCl in MeOH (70 mL) and the resulting solution was stirred (rt, 14 h). The reaction mixture was concentrated in vacuo. The resulting solid was dissolved in DCM (100 mL) and sat. NaHCO3 (50 mL) was added. A solid formed and was filtered to afford the title compound as a white solid (1.4 g, 94%). MS (ESI): mass calcd. for C10H8O4, 192.04; m/z found, 193.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.24 (s, 1H), 7.77 (d, J=8.5, 1H), 6.94 (d, J=1.4, 1H), 6.86 (dd, J=8.5, 1.7, 1H), 3.90 (s, 3H).

Provenance & Evidence