A strategy to avoid anomalous  O ‐alkylation of 4‐hydroxyindole by diethyl bromomalonate | Zendy

Papageorgiou George | Zendy; Corrie John E. T. | Zendy

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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

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.

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