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Synlett 1992; 1992(9): 737-738
DOI: 10.1055/s-1992-21474
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Tandem Cohalogenation-Dehydrohalogenation: A New Efficient Synthesis of 2-Acylfurans from α,β-Unsaturated Ketones

J. -P. Dulcère* , R. Faure, J. Rodriguez
  • *Laboratoire de Synthèse Organique, SM3B URA 1411, Université d'Aix-Marseille III, Faculté des Sciences de St. Jérôme, D 12, avenue Escadrille Normandie-Niemen, F-13397 Marseille Cedex 13, France
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Publication Date:
08 March 2002 (online)

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Cohalogenation of methyl vinyl ketone by N-bromosuccinimide (NBS) in alcohols affords regioselectively β-alkoxy-α-bromobutanones 1a-d which are converted in a one-pot process by dehydrohalogenation with 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU) into 2-acetyl-4-alkoxymethyl-5-methylfurans 2a-d.

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