Water → 9-ethyl-9H-carbazole-3,6-dicarbaldehyde

Participants

Reaction Conditions

Reaction Steps

LiAlH4 (2.15 g, 56.3 mmol) is added portionwise to a suspension of N-ethylcarbazole-3,6-dicarboxylic acid (5.7 g, 20.12 mmol) in 160 ml of anhydrous THF cooled to 0° C. The suspension is stirred for 1 h 30 min at room temperature and then 1 hour under reflux. After cooling to 0° C., the excess hydride is hydrolyzed with a little water and the salts are filtered off. The filtrate is evaporated to dryness and dried under vacuum to give a yellow solid. The latter is suspended in dichloromethane in the presence of activated manganese dioxide (4 g, 15.16 mmol), and the mixture is stirred overnight at room temperature. 4 g of activated manganese dioxide are added and the mixture is stirred for a further 24 h. The suspension is filtered and the filtrate is evaporated under vacuum to give the expected product.

Provenance & Evidence