Methanol → Methyl 3-methyl-2-benzofurancarboxylate

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.

1. stirringThe reaction mixture was stirred overnight at room temperature
2. concentrationconcentrated
3. dissolutiondissolved in ethyl acetate (100 ml)
4. washwashed with aqueous sodium bicarbonate solution (100 ml)
5. dry with materialThe organic layer was dried over sodium sulfate
6. concentrationconcentrated

ORD record

ord-c6b527b2c1074afab8ad5326b4ecda9b

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07368572B2