Ethyl Acetate → 5-Methoxy-1H-indole-2-carbaldehyde

Participants

Reaction Steps

Under nitrogen atmosphere, to a solution of 5-methoxyindole-2-carboxylic acid (1.00 g) in Et2O (40 mL) was added LiAlH4 (280 mg) at 0° C., and the mixture was stirred under reflux for 3 hours. The mixture was treated with ethyl acetate, diluted with an aqueous hydrochloric acid solution, and extracted with ethyl acetate. The mixture was concentrated to give a crude alcohol compound (840 mg, 91%), which was dissolved in THF (10 mL), and stirred with MnO2 (4.20 g) at room temperature for 5 hours. The mixture was filtered on celite, and the filtrate was concentrated, and the residue was purified by silica gel column chromatography to give 5-methoxyindole-2-carbaldehyde (300 mg, 36%).

Provenance & Evidence