THE CHEMISTRY OF THE INDOLE GRIGNARD REAGENT: I. THE REACTION OF INDOLE MAGNESIUM IODIDE WITH ETHYL CHLOROFORMATE

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Abstract
In contrast to previous reports in the literature, it has been shown that both 1- and 3-carbethoxyindole are obtained from the reaction of indole magnesium iodide with 1 or 2 moles of ethyl chloroformate. The formation of 1-carbethoxyindole was favored at low temperatures (i.e. −10°), whereas maximum yields of 3-carbethoxyindole were obtained at 10°. Significant quantities of 1,3-dicarbethoxyindole are only formed in the presence of 2 equivalents of ethyl chloroformate and when the reaction is carried out at higher temperatures (i.e. 35°).Paper and gas–liquid chromatographic systems have been developed for the qualitative and quantitative analysis of mixtures containing indole, 1-, 2-, and 3-carbethoxyindole, and 1,3-dicarbethoxyindole.

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