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

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.

Keywords:

• Aldehyde homologation
• diethyl methylformyl-2-phosphonate dimethylhydrazone

ACKNOWLEDGMENT

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

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