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

Autor:	Richard J. Petroski
Rok vydání:	2010
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Chemistry Reagent Yield (chemistry) Aqueous acetone Organic Chemistry Organic chemistry Phosphonate Aldehyde Derivative (chemistry)
Zdroj:	Synthetic Communications. 41:63-66
ISSN:	1532-2432 0039-7911
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6dd67cc543356387d70ecb416be47909 https://doi.org/10.1080/00397910903531797 Zobrazit plný text záznamu