Sodium borohydride → Tryptophol

Participants

Reaction Steps

A suspension of benzyl 3-indolylglyoxylate (55.8 g.) and sodium borohydride (22.7 g.) in isopropanol (560 ml.) was heated to reflux over a period of 40 minutes and stirred at that temperature for 4 hours. After cooling the mixture was diluted with water (1.2 l.) and extracted with dichloromethane. The extract was washed with water and the solvent evaporated under reduced pressure to yield a viscous oil. This was distilled at 0.5 - 1 mm. pressure and the friction which distilled at a vapour temperature of 160°-190° was crystallised from toluene (100 ml.), giving the title compound as white crystals, mp. 57°-90°. Yield 24.3 g. (75.5%).

Provenance & Evidence