Iodoethane → 5-Ethoxy-1H-indole

Participants

Reaction Conditions

Reaction Steps

A mixture of commercially available 5-hydroxy-indole (18 g, 13.5 mmol), anhydrous K2CO3 (93.5 g, 5 equiv) and iodoethane (40.5 ml, 3.75 equiv) in acetone (180 mL) is stirred at 50° C. under argon. When TLC (dichloromethane-methanol, 95:5) indicates the disappearance of 5-hydroxy-indole (4 days), the mixture is filtered, the solid is washed with acetone, then the filtrate is concentrated to give 17.67 g (90%) of the title compound, which is sufficiently pure to be used in the next step. M.p. 144-146° C. (from ethanol).

Provenance & Evidence