Dimethylformamide → 1,4,6-Trimethyl-1H-indole-3-carbaldehyde

Participants

Reaction Steps

A solution of 1,4,6-trimethyl-1H-indole (800 mg, 5 mmol) in DMF (0.9 mL) is cooled to 5° C. under nitrogen. Pyrophosphoryl chloride (1.4 mL, 10 mmol) is then slowly introduced. Upon complete addition the cooling bath is removed and the reaction is allowed to warm to ambient temperature. After a total of 45 minutes, the reaction is recooled to 5° C. and is slowly quenched with 2N NaOH. The pH of the solution is adjusted to 8. The precipitated solid is collected by filtration and is washed with water to afford 1,4,6-Trimethyl-1H-indole-3-carbaldehyde (875 mg, 93%).

Provenance & Evidence