Dimethylformamide → Methyl 1-ethyl-3-formyl-1H-indole-6-carboxylate

Participants

Reaction Steps

1-Ethyl-1H-indole-6-carboxylic acid methyl ester (900 mg, 4.45 mmol) was dissolved in DMF (3.3 mL). This was added dropwise to an ice-cold solution of POCl3 (430 μL, 4.5 mmol) in DMF (1.5 mL). The reaction mixture was stirred at room temperature for 90 minutes. The reaction mixture was then treated with 6N NaOH (3.5 ml). The mixture was then partitioned between H2O and ethyl acetate. Purification by silica gel chromatography (5-10% EtOAc/CH2Cl2) yielded 1-ethyl-3-formyl-1H-indole-6-carboxylic acid methyl ester (985 mg, 96%) as a white solid.

Provenance & Evidence