An Efficient Approach to the Synthesis of Ethyl α-Cyanoalkyl β-Substituted Acrylates by the HWE Olefination of Ethyl 2-(Diethoxyphosphoryl) Cyanoalkanoates

Abstract

Ethyl α-cyanoalkyl β-substituted acrylates 5a–i were prepared in good yields on a synthetic scale by Horner–Wadsworth–Emmons olefination of the corresponding ethyl 2-(diethoxy-phosphoryl) cyanoalkanoates 3a–c using different aldehydes and anhydrous potassium carbonate in dry THF at reflux.

Keywords:

• Ethyl α-cyanoalkyl β-substituted acrylates
• ethyl 2-(diethoxyphosphoryl) cyanoalkanoates
• Horner–Wadsworth–Emmons reaction
• triethyl phosphonoacetate

Notes

*Determined by ¹H NMR spectral analysis.