2-Methoxyethanol → HCID 66779368, compound

Participants

Reaction Steps

To a solution (25 mL) of 2-methoxyethanol (2.74 mL) in N,N-dimethylformamide was added sodium hydride (60%, oily, 835 mg) at 0° C., and the mixture was stirred at room temperature for 30 min. After stirring, a solution (25 mL) of methyl 3-(bromomethyl)-5-fluoro-1-benzofuran-2-carboxylate (5.00 g) synthesized in Example A47(2) in N,N-dimethylformamide was added at 0° C. The reaction mixture was stirred at 80° C. for 5 hr, then saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-40% ethyl acetate/hexane) to give the title object compound (1.54 g, 31%) as a pale-yellow oil.

Provenance & Evidence