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Note | Regular issue | Vol 60, No. 12, 2003, pp.2761-2765
Published online, 14th October, 2003
DOI: 10.3987/COM-03-9879
Synthesis of 5-Substituted Indole Derivatives, Part 5. A Synthesis of 5-Formyl-1H-indole-2-carboxylates: The CH2SO3H Functionality as a Masked Formyl Group

Béla Pete,* Gyula Parlagh, and László Töke

*Department of Organic Chemical Technology, Technical University of Budapest, H-1521 Budapest, Gellért tér 4, Hungary


New synthetic intermediates, ethyl 5-formyl-1H-indole-2-carboxylates (4) were prepared from 2-ethoxycarbonyl-1H-indole-5-methanesulfonic acids (1). The transformation of the sulfomethyl group to formyl function was accomplished through elimination of SO2 to yield ethyl 5-chloromethyl-1H-indole-2-carboxylates (2), hydrolysed to ethyl 5-hydroxymethyl-1H-indole-2-carboxylates (3), then oxidized to aldehydes (4).