Water → 3,5-Dimethyl-1-benzofuran-2-carbaldehyde

Participants

Reaction Steps

To a solution (50 mL) of N-methoxy-N,3,5-trimethyl-1-benzofuran-2-carboxamide (3.78 g) synthesized above in tetrahydrofuran was added lithium aluminum hydride (307 mg) at −78° C., and the mixture was stirred for 2 hr. Water (350 μL) was added to quench the reaction, 1N aqueous sodium hydroxide solution (700 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 washed with hexane to give the title object compound (2.08 g, 74%) as a yellow solid.

Provenance & Evidence