Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-hydroxy-benzofuran-3-one (5.0 g, 33.3 mmol) in xylene (100 mL) was added methyl (triphenylphosphoranylidene)acetate (11.1 g, 33.3 mmol) and the resulting reaction mixture was heated (120° C., 24 h). The reaction mixture was concentrated in vacuo and the residue was treated with 1 M HCl adjusting the pH to 3. The organic layer was extracted with EtOAc (2×100 mL). The combined organic layers were dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using EtOAc:hexane (0-70%) to provide the title compound as a clear oil (1.6 g, 23%). MS (ESI): mass calcd. for C10H10NO4, 206.2; m/z found, 207.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.03-7.07 (m, 1H), 7.37 (d, J=8.4, 1H), 6.93 (d, J=2.2, 1H), 6.77 (dd, J=8.4, 2.2, 1H), 5.20 (br s, 1H), 3.74 (s, 3H), 3.67 (s, 2H).

Provenance & Evidence