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Synthesis 2015; 47(05): 672-678
DOI: 10.1055/s-0034-1378940
DOI: 10.1055/s-0034-1378940
paper
Base-Mediated Addition of 1-(2-Hydroxyalkyl)pyrroles to Acetylene: Atom-Economic Route to 1-[2-(Vinyloxy)alkyl]pyrroles
Further Information
Publication History
Received: 05 August 2014
Accepted after revision: 06 November 2014
Publication Date:
15 December 2014 (online)
Abstract
Nucleophilic addition of 1-(2-hydroxyalkyl)pyrroles to acetylene, an unactivated carbon–carbon triple bond, in the presence of a base has been studied. As a result an atom-economic synthetic method to obtain 1-[2-(vinyloxy)alkyl]pyrroles in good yields employing superbase, sodium or potassium hydroxide in dimethyl sulfoxide, systems has been developed. 1-[2-(Vinyloxy)alkyl]pyrroles are cleaved by base with the elimination of vinyl alcohol to give 1-vinylpyrroles.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378940.
- Supporting Information
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