Water → Ethyl 6-(Benzyloxy)benzofuran-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzyloxy-2-hydroxy-benzaldehyde (10.0 g, 44 mmol) in DMF (400 mL) is added K2CO3 (18.6 g, 131 mmol) followed by bromo-acetic acid ethyl ester (5.4 mL, 8.1 g, 48 mmol) and the resulting mixture was heated (80° C., 12 h). The reaction mixture was cooled (rt) and treated with H2O (200 mL). The solid was filtered to afforded the title compound as a beige solid (8.1 g, 62%). MS (ESI): mass calcd. for C18H16O4, 296.1; m/z found, 297.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.53 (d, J=8.7, 1H), 7.48-7.30 (m, 6H), 7.12 (d, J=2.0, 1H), 7.01 (dt, J=6.1, 3.1, 1H), 5.09 (d, J=28.6, 2H), 4.42 (q, J=7.1, 2H), 1.37 (dt, J=36.6, 9.6, 3H).

Provenance & Evidence