Jump to content

Triethyl phosphonoacetate

From Wikipedia, the free encyclopedia
Triethyl phosphonoacetate
Names
Preferred IUPAC name
Ethyl (diethoxyphosphoryl)acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.598 Edit this at Wikidata
UNII
  • 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
  • CCOC(=O)CP(=O)(OCC)OCC
Properties
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 checkY☒N ?)

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

[edit]
  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.