Ethyl Acetate → Indole-5-carboxaldehyde

Participants

Reaction Steps

Indole-5-carboxylic acid (3.10 g) was dissolved in tetrahydrofuran (50 ml), and lithium aluminium hydride (1.50 g) was added thereto, followed by heating under reflux for 20 hours. The reaction solution was cooled to room temperature, and ethyl acetate and then a 2N aqueous solution of sodium hydroxide were added thereto to cease the reaction. The reaction solution was dried over anhydrous sodium sulfate and insoluble matters were filtered off. Manganese dioxide (30.00 g) was added to the filtrate, followed by stirring at room temperature for 96 hours. Insoluble matters were filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give indole-5-carbaldehyde (1.43 g).

Provenance & Evidence