Triethyl phosphonoacetate

Triethyl phosphonoacetate
Names
	IUPAC name Ethyl 2-diethoxyphosphorylacetate
Identifiers
CAS Number	867-13-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	12776 ;
ECHA InfoCard	100.011.598
PubChem CID	13345;
UNII	022826171T ;
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 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 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).
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	Infobox references

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

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]

References

Rathke, Michael W.; Nowak, Michael (July 1985). "The Horner-Wadsworth-Emmons modification of the Wittig reaction using triethylamine and lithium or magnesium salts". The Journal of Organic Chemistry. 50 (15): 2624–2626. doi:10.1021/jo00215a004.

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[1] Rathke, Michael W.; Nowak, Michael (July 1985). "The Horner-Wadsworth-Emmons modification of the Wittig reaction using triethylamine and lithium or magnesium salts". The Journal of Organic Chemistry. 50 (15): 2624–2626. doi:10.1021/jo00215a004.