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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2010 - Issue 1
139
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Original Articles

New Preparation of Diethyl Methylformyl-2-phosphonate Dimethylhydrazone: A Reagent for Aldehyde Homologation

Pages 63-66 | Received 08 Sep 2009, Published online: 14 Dec 2010
 

Abstract

The phosphonate reagent diethyl methylformyl-2-phosphonate dimethylhydrazone contains a protected aldehyde group instead of the usual ester group. It can be used for the two-carbon homologation of aldehydes to α, β-unsaturated aldehydes. The reagent can be prepared in good overall yield (82%) and purity by deprotection of commercially available diethyl-2,2-(diethoxy)ethylphosphonate with p-toluenesulfonic acid in 1.5% aqueous acetone to give diethyl formylmethyl-2-phosphonate, followed by a simple preparation of the dimethylhydrazone derivative with N,N-dimethylhydrazine.

ACKNOWLEDGMENT

I thank Karl Vermillion of the National Center for Agricultural Utilization Research for acquisition of NMR data.

Notes

The mention of trade names or commercial products in this article is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the U.S. Department of Agriculture.

This article is not subject to U.S. copyright laws.

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