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Synthesis 2001(13): 2003-2006
DOI: 10.1055/s-2001-17714
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-Alkyl-2,5-dimethylfuran Derivatives by Indirect Alkylation of 2,5-Dimethylfuran with Aliphatic Nitrocompounds

Roberto Ballini*, Giovanna Bosica, Dennis Fiorini, Guido Giarlo
Dipartimento di Scienze Chimiche dell"Università, Via S. Agostino 1, 62032 Camerino (MC), Italy
Fax: +39(737)637345; e-Mail: ballini@camserv.unicam.it;
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Publication History

Received 20 June 2001
Publication Date:
10 August 2004 (online)

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Abstract

The preparation of 3-alkyl-2,5-dimethylfuranes via indirect alkylation of 2,5-dimethylfuran is reported. Thus, primary nitroalkanes react with cis-3-hexen-2,5-dione giving a tandem Michael addition/elimination of nitrous acid, followed by chemoselective hydrogenation of the C=C double bond of the obtained enones. The Paal-Knorr reaction, performed with p-toluenesulfonic acid in diethyl ether, completes the formation of the title compounds. In this context the nitroalkane can be considered as an alkyl cation synthon.

Key words

furan - nitroalkanes - Michael reaction - heterocyclization

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