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

Participants

Reaction Steps

To a solution (100 mL) of methyl 5-methoxy-3-methyl-1-benzofuran-2-carboxylate (5.00 g) in tetrahydrofuran was added lithium aluminum hydride (862 mg) at 0° C., and the mixture was stirred for 1.5 hr. Water (860 μL) was added to quench the reaction, 1N aqueous sodium hydroxide solution (860 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 to give a pale-yellow solid. To a solution of the obtained solid in tetrahydrofuran (80 mL) was added active manganese dioxide (21.2 g), and the mixture was stirred at 50° C. overnight. Manganese dioxide was filtered off, and the filtrate was concentrated under reduced pressure to give the title object compound (3.41 g, 79%) as a brown solid.

Provenance & Evidence