Methanol → Methyl 3-methyl-2-benzofurancarboxylate

Participants

Reaction Steps

To a solution of 3-methyl-benzofuran-2-carboxylic acid (0.98 g, 5.6 mmol) and catalytic amount of DMF (5 drops) in THF (25 ml) was added oxalyl chloride (0.53 ml, 6.1 mmol). After stirring the solution for 1 h at room temperature, methanol (20 ml) and TEA (7.0 ml) were added. The reaction mixture was stirred overnight at room temperature, then concentrated and dissolved in ethyl acetate (100 ml) and washed with aqueous sodium bicarbonate solution (100 ml). The organic layer was dried over sodium sulfate and concentrated to provide crude methyl 3-methylbenzofuran-2-carboxylate (1.0 g, 5.3 mmol) as a tan solid, which was used without further purification.

Provenance & Evidence