Dimethyl Sulfoxide → METHYL 7-HYDROXY-2-NAPHTHOATE

Participants

Reaction Steps

Treat a mixture containing trifluoromethanesulfonic acid 7-(1-ethyl-1-hydroxypropyl)naphthalen-2-yl ester (0.41 g, 14.1 mmol), Pd(OAc)2 (0.30 g, 1.38 mmol), bis-(diphenylphosphino)ferrocene (0.705 g, 1.27 mmol), Et3N (10.2 mL, 73.2 mmol), in MeOH (12 mL) and DMSO (18 mL) with carbon monoxide at 100 psi at 80° C. for 4 h. Pour the reaction mixture into ether (300 mL) and wash with brine (5×100 mL). Add EtOAc (250 mL), wash the organic layer with brine, dry over Na2SO4, and filter. Concentrate the filtrate to give the title compound as a tan solid (2.84 g, quant). 1H NMR (400 MHz, CDCl3) δ 3.98 (s, 3H), 7.23-7.29 (m, 2H), 7.78 (t, J=8.3 Hz, 2H), 7.88-7.90 (m, 1H), 8.43 (d, J=0.88 Hz, 1H).

Provenance & Evidence