Water → 5-Chloro-3-methyl-1-benzofuran-2-carbaldehyde

Participants

Reaction Steps

To a solution (40 mL) of 5-chloro-N-methoxy-N,3-dimethyl-1-benzofuran-2-carboxamide (2.15 g) synthesized above in tetrahydrofuran was added lithium aluminum hydride (322 mg) at 0° C., and the mixture was stirred for 1 hr. Water (320 μL) was added to quench the reaction, 1N aqueous sodium hydroxide solution (320 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 (tetrahydrofuran) to give a pale-yellow solid. The obtained solid was washed with diisopropyl ether to give the title object compound (1.21 g, 73%) as a pale-yellow solid.

Provenance & Evidence