3095-95-2

clear colorless to yellow viscous liquid

Diethylphosphonoacetic Acid (DPA) is a Horner-Wadsworth-Emmons (HWE) reagent. The mixed anhydride of trifluoroacetic acid—diethylphosphonoacetic acid Treat a 21-hydroxy-20-keto steroid leads directly to cardenolides by an intramolecular Horner-Emmons reaction. It could also used as a dummy template to prepare a molecularly imprinted polymer  for use as an artificial receptor for organophosphorus pesticides (OPPs)[1-3].

Diethylphosphonoacetic Acid is a reagent that is used for enantioselective preparation of α-phosphoryl-α,β-unsatd.-δ-aryl-δ-lactones from nonracemic β-hydroxyaldehydes and their conversion to α-methylene-δ-aryl-δ-lactones.

Diethylphosphonoacetic acid is synthesised using triethyl phosphonoacetate as a raw material by chemical reaction. The specific synthesis steps are as follows:
After dissolving triethyl phosphonoacetate (1.7 g, 7.5 mmol) in ethanol / water (15 mL ie 14: 1) at room temperature, potassium hydroxide (424.2 mg, 7.56 mmol, ) 6597-4400) was added and stirred at room temperature. The reaction was neutralized with 1N HCl to pH 4, the ethanol was removed by distillation under reduced pressure, diluted with chloroform (20 mL), washed with water (10 mL) and saturated brine (10 mL). The separated organic layer was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to obtain 2-(diethoxyphosphoryl)acetic acid 4 (1.48 gm, 100percent).

Journal of the American Chemical Society, 102, p. 4534, 1980 DOI: 10.1021/ja00533a047

reaction type: C-C Bond Formation

[1] S. Donovan, J. Mcmurry, M. Avery. “Synthesis of digitoxigenin by remote functionalization.” Tetrahedron Letters 20 1 (1979): 3287–3290.
[2] A. M. Boldi, Hisham O. Eissa, Charles R. Johnson. “Solid-phase library synthesis of triazolopyridazines via [4+2] cycloadditions.” Tetrahedron Letters 40 1 (1999): 619–622.
[3] Lu Zhang. “Preparation and Characterization of Broad-Spectrum Artificial Antibody for OPPs Based on Dummy Template Imprinting Technique.” International Journal of Polymer Analysis and Characterization 117 1 (2014): 510–521.