Synthesis of 2-(Thiophen-3-yl)vinylphosphonic Acid

Abstract

A simple and efficient synthesis of 2-(thiophen-3-yl)vinylphosphonic acid has been developed. The title compound is obtained in 70% yield by addition of thiophene-3-carbaldehyde to lithium diethyl methylenephosphonate, followed by dehydration and hydrolysis. ¹H, ¹³C, and ³¹P NMR spectra are presented for each of the intermediates.

Keywords:

• Diethyl methylphosphonate
• 2-(thiophen-3-yl)vinylphosphonic acid
• thiophene-3-carbaldehyde

ACKNOWLEDGMENTS

We are grateful to Consejo Nacional de Ciencia y Tecnología (CONACYT) for financial support through grants 48356-Q and C02-44704. We are indebted to Graciela I. González-Castillo for technical support and Dr. Herbert Höpfl for many important observations.