The synthesis of 2-(indol-3-yl) ethane derivatives

In this project, tryptophol was made by reaction of indole with oxalyl chloride followed by esterification with ethanol and reduction of the ester with lithium aluminum hydride. The halogen, benzoate, and tosylate derivatives of tryptophol were obtained.The attempted synthesis of the 2-(indol-3-yl)ethyl azide via benzoate and tosylate of tryptophol were singularly unsuccessful. However, it was possible to arrive at the azide by nucleophilic substitu­tion of both 2-(indol-3-yl)ethyl iodide and 2-(indol-3-yl)ethyl bromide.The photolysis and thermolysis of the azide resulted in similar decomposition to one or more products which could not be identified. In addition v-triazoles were pre­pared by allowing the azide to react with methyl propiolate and dimethyl acetylenedicarboxylatePhysical constants for all these derivatives were obtained and analyzed in this work.