Synthesis 2008(8): 1221-1226  
DOI: 10.1055/s-2008-1067002
PAPER
© Georg Thieme Verlag Stuttgart · New York

Development of a Robust and Practical Process for the Darzens Condensation and α,β-Epoxide Rearrangement: Scope and Limitations of the Methodology

Jeremy Malcolm Zimbron, Manuela Seeger-Weibel, Hans Hirt, Fabrice Gallou*
Novartis Pharma AG, Chemical and Analytical Development, 4002 Basel, Switzerland
Fax: +41(61)6962711; e-Mail: fabrice.gallou@novartis.com;
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Publikationsverlauf

Received 19 December 2007
Publikationsdatum:
27. März 2008 (online)

Abstract

A practical and robust process for the Darzens condensation of substituted benzaldehydes and subsequent α,β-epoxy rearrangement is reported. The process developed is both amenable to large scale and parallel synthesis. While electron-poor benzaldehydes gave mixtures of aryl ketones and 2-substituted aryl ketones in mediocre to low yields, electron-rich benzaldehydes were found to react in high yields with complete regioselectivity to form 2-substituted aryl ketones.

1

Current address: University of Neuchâtel, AV. BelleVaux 51, CP 2, 2007 Neuchâtel, Switzerland; jeremy.zimbron@unine.ch.

2

Hirt H., Haenggi R., Reyes J., Seeger-Weibel M., Gallou F.; Org. Process Res. Dev. 2008, 12, 111