Premium
A strategy to avoid anomalous O ‐alkylation of 4‐hydroxyindole by diethyl bromomalonate
Author(s) -
Papageorgiou George,
Corrie John E. T.
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420610
Subject(s) - chemistry , alkylation , acetone , potassium carbonate , potassium , diethyl carbonate , indole test , organic chemistry , nitrogen , medicinal chemistry , catalysis , ethylene carbonate , electrode , electrolyte
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.