Journal of heterocyclic chemistry

A strategy to avoid anomalous O??alkylation of 4??hydroxyindole by diethyl bromomalonate

G Papageorgiou, JET Corrie

Index: Papageorgiou, George; Corrie, John E. T. Journal of Heterocyclic Chemistry, 2005 , vol. 42, # 6 p. 1101 - 1104

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Citation Number: 2

Abstract

Abstract Alkylation of 4-hydroxyindole with diethyl bromomalonate under standard conditions (potassium carbonate-acetone) gave the expected indolyloxymalonate ester 3 together with the anomalous indolyloxy-2-bro-momalonate 4. Depending on conditions, the ratio of the two products varied between 4: 1 and 1: 2. Protection of the indole nitrogen by a carbobenzyloxy group eliminated formation of the anomalous product.