Oxygen → 4-(1H-indol-3-yl)butan-1-ol

Participants

Reaction Steps

LiAlH4 (1.14 g, 30 mmol) was initially introduced into dry THF (100 ml) with exclusion of oxygen. 4-(1H-Indol-3-yl)butanoic acid (2.03 g, 10 mmol, dissolved in 80 ml of dry THF) was added dropwise to the suspension in the course of 30 min. Thereafter, the mixture was heated under reflux at the boiling point for 3 h. The reaction mixture was stirred at room temperature overnight. Water (30 ml) was then cautiously added to the mixture. The mixture was stirred for 20 min and 2N NaOH (10 ml) was added. The organic phase was separated off and the aqueous solution which remained was extracted with diethyl ether (3×40 ml). The ethereal solution was dried over Na2SO4 and concentrated to dryness on a rotary evaporator. Ind-57 was obtained in this way in a yield of 1.8 g

Provenance & Evidence