Synthesis 2015; 47(05): 672-678
DOI: 10.1055/s-0034-1378940
paper
© Georg Thieme Verlag Stuttgart · New York

Base-Mediated Addition of 1-(2-Hydroxyalkyl)pyrroles to Acetylene: Atom-Economic Route to 1-[2-(Vinyloxy)alkyl]pyrroles

Evgeny Kh. Sadykov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   eMail: esad@irioch.irk.ru
,
Natalya A. Lobanova
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   eMail: esad@irioch.irk.ru
,
Valery K. Stankevich
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   eMail: esad@irioch.irk.ru
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Publikationsverlauf

Received: 05. August 2014

Accepted after revision: 06. November 2014

Publikationsdatum:
15. Dezember 2014 (online)


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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.

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