5-Methoxyindoleacetic acid → 5-Methoxytryptophol

Participants

Reaction Steps

A solution of 15 g of (5-methoxyindol-3-yl)acetic acid (0.073 mol) in 100 ml of tetrahydrofuran is added to a suspension of 2.1 g (0.219 mol) of lithium aluminum hydride in 100 ml of ethyl ether and the reaction mixture is brought to reflux for 6 hours. The reaction mixture is then hydrolyzed with 80 ml of a saturated aqueous magnesium sulfate solution. The whole mixture is filtered through celite and the solvents are evaporated under vacuum. The residue is taken up in a small amount of water and extracted a number of times with dichloromethane. The product is obtained after evaporation of the solvant.

Provenance & Evidence