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United States Department of Agriculture

Agricultural Research Service

Research Project: IDENTIFICATION AND PRACTICAL USE OF SEMIOCHEMICALS FOR THE MANAGEMENT OF AGRICULTURALLY IMPORTANT INSECTS

Location: Crop Bioprotection Research

Title: New preparation of diethyl methylformylphosphonate dimethylhydrazone: A reagent for aldehyde homologation

Author
item Petroski, Richard

Submitted to: Synthetic Communications
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: December 5, 2009
Publication Date: December 14, 2010
Citation: Petroski, R.J. 2010. New preparation of diethyl methylformylphosphonate dimethylhydrazone: A reagent for aldehyde homologation. Synthetic Communications. 41:63-66.

Interpretive Summary: The use of insect pheromones has become an important part of the process to develop more efficient pest and weed control strategies, because of cost savings and selectivity. Difficulties occur when the chemical synthesis of the pheromone substances is lengthy or expensive. This paper describes a better method to prepare a vital reagent chemical, required to shorten a commonly used linear synthetic sequence from three expensive steps to just two much less expensive steps. The research was conducted in response to the expressed needs of our “customers” and stakeholders. These results are important to scientists, especially those in industry, because synthetic pathways must be economical and capable of scale-up in order to be commercially viable.

Technical 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 a, ß-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.

Last Modified: 7/25/2014
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