Sodium Carbonate → 5-Benzofurancarboxylic acid, 3-methyl-, methyl ester

Participants

Reaction Conditions

Reaction Steps

Methyl 4-(allyloxy)-3-iodobenzoate (587 mg, 1.84 mmol) is combined with Pd(OAc)2 (5%, 20 mg, 0.1 mmol), Na2CO3 (487 mg, 4.6 mmol), sodium formate (125 mg, 1.8 mmol) and n-Bu4NCl.H2O (561 mg, 2.0 mmol) in DMF (5 mL) and heated to 80° C. for 2 days. The mixture is concentrated under high vacuum and partitioned between 50% saturated NaCl (10 mL) and CH2Cl2 (4×10 mL). The combined organics are washed with 5% HCl (10 mL), dried (Na2SO4) and concentrated to a brown oil. The crude material is chromatographed over 15 g slurry-packed silica gel, eluting with 15% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 153 mg (44%) of methyl 3-methyl-1-benzofuran-5-carboxylate as a white solid. HRMS (FAB) calcd for C11H10O3+H: 191.0708, found: 191.0705 (M+H)+.

Provenance & Evidence