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A new and efficient synthesis of 2-trifluoromethyl substituted pyrroles and ethyl-2,3-bis(ethoxycarbonyl)-1H-pyrrole-1-propionate

✍ Scribed by Michael G. Hoffmann; Ernest Wenkert

Publisher: Elsevier Science
Year: 1993
Tongue: French
Weight: 355 KB
Volume: 49
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)86286-4

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✦ Synopsis

Dirhodium tetraacetate catalyzed decomposition of trifluoromethyl acetyl diazoacetates 6a and 6b in ethyl vinyl ether gives rise to the dihydrofuroates 7a and 7b, respectively, which can be converted into the corresponding 2-(trifluoromethyl)pyrroles. This two step pyrrole synthesis is also suitable for the preparation of ethyl 2,3-bis(ethoxycarbonyl)-1 H-pyrrole-1 -propinate, an important intermediate for the synthesis of necin bases.

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