Triethyl phosphonoacetate

Triethyl phosphonoacetate is a reagent for organic synthesis used in the Horner-Wadsworth-Emmons reaction (HWE) or the Horner-Emmons modification.

Triethyl phosphonoacetate

Names
Preferred IUPAC name Ethyl (diethoxyphosphoryl)acetate
Identifiers
CAS Number	867-13-0 Y
3D model (JSmol)	Interactive image
ChemSpider	12776 N
ECHA InfoCard	100.011.598
PubChem CID	13345
UNII	022826171T Y
CompTox Dashboard (EPA)	DTXSID4041573
InChI InChI=1S/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3 N Key: GGUBFICZYGKNTD-UHFFFAOYSA-N InChI=1/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3 N Key: GGUBFICZYGKNTD-UHFFFAOYAB
SMILES CCOC(=O)CP(=O)(OCC)OCC
Properties
Chemical formula	C8H17O5P
Molar mass	224.19 g/mol
Boiling point	142 to 145 °C (288 to 293 °F; 415 to 418 K) at 9 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Triethyl phosphonoacetate can be added dropwise to sodium methoxide solution to prepare a phosphonate anion. It has an acidic proton that can easily be abstracted by a weak base. When used in an HWE reaction with a carbonyl the resulting alkene formed is usually the E alkene, and is generated with excellent regioselectivity.^[1]