Sodium → 4-Methoxymethyl-indole

Participants

Reaction Steps

A solution of 2.84 g of sodium in 155 ml of ethanol is dripped within 10 minutes into a solution of 15.57 g of 4-methoxymethyl-1-tosylindole in 155 ml of ethanol, whereupon the mixture is heated with reflux for 11/2 h; next it is cooled, stirred into 1.5 liters of half-saturated ice-cold sodium-di-hydrogen-phosphate solution, extracted with ethyl acetate; whereupon, the ethyl-acetate extracts are washed neutral with water. After the solvent has been distilled off, the raw product is chromatographed on silical gel with hexane/ethyl-acetate (0-20%). 6.2 g of 4-methoxymethyl-indole is obtained in the form of a colorless oil.

Provenance & Evidence