Water → 6-Fluoro-3-methyl-1-benzofuran-2-carbaldehyde

Participants

Reaction Steps

To a solution (50 mL) of 6-fluoro-N-methoxy-N,3-dimethyl-1-benzofuran-2-carboxamide (3.65 g) synthesized above in tetrahydrofuran was added lithium aluminum hydride (292 mg) at 0° C., and the mixture was stirred for 1 hr. Water (300 μL) was added to quench the reaction, 1N aqueous sodium hydroxide solution (600 μL) was added, and the mixture was stirred at room temperature for 1 hr. The resulting insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the title object compound (1.88 g, 69%) as a pale-yellow solid.

Provenance & Evidence