Triethyl phosphonoacetate

CAS 867-13-0, Cat. No EN300-52552

Reagent for Horner–Wadsworth–Emmons reaction

Triethyl phosphonoacetate is a reagent for Horner–Wadsworth–Emmons reaction. It's a liquid that with proper storage conditions a shelf stable. Through deprotonation by diverse bases, it yields a carbanion capable of reacting with carbonyl compounds, resulting in alkene formation. Notably, the reaction showcases a preference for the E-isomer, although this selectivity tends to be less pronounced with ketones compared to aldehydes. In the case of sensitive substances, the Horner-Wadsworth-Emmons reaction (HWE) can be carried out under Masamune-Roush conditions. This entails utilizing LiCl and DBU in acetonitrile, allowing for the successful transformation of these substrates into desired products.

Synonyms: Acetic acid, (diethoxyphosphinyl)-, ethyl ester (9CI), Acetic acid, phosphono-, triethyl ester (6CI, 7CI, 8CI), (Diethoxyphosphinyl)acetic acid ethyl ester, (Diethoxyphosphoryl)acetic acid ethyl ester, (Ethoxycarbonylmethyl)diethoxyphosphine oxide, 2-(Diethoxyphosphinyl)acetic acid ethyl ester, 2-Phosphonoacetic acid triethyl ester, Carbethoxymethyldiethyl phosphonate, Diethyl 2-ethoxy-2-oxoethylphosphonate, Diethyl carbethoxymethylphosphonate, Diethyl ethoxycarbonylmethanephosphonate, Diethyl phosphonoacetic acid ethyl ester, Ethyl (diethoxyphosphinyl)acetate