Water → N-[2-(1-Oxobutyl)phenyl]acetamide

Participants

Reaction Steps

A solution of 2-methyl-3-propylindole (159 g) in methanol (1370 ml) was stirred under nitrogen while a solution of sodium periodate (430.4 g) in water (2450 ml) was added over a period of one hour. External cooling was applied as necessary to maintain the reaction temperature at or below 25°. After stirring at room temperature overnight, the mixture was diluted with water (7 liters) and was extracted with dichloromethane (2 liters). The phases were separated, and the aqueous layer was extracted twice more with dichloromethane (1 liter each). The combined organic phases were washed twice with water (1.5 liter each), dried (MgSO4), and evaporated to provide 246.5 grams of crude product. This material was purified by two successive chromatographies over flash silica gel, eluting the desired product with dichloromethane. Upon evaporation of the appropriate fractions, there was obtained 160.6 grams (85% yield) of the title compound as a white crystalline solid, m.p. 46.5°-47°.

Provenance & Evidence