tert-Butyl diethylphosphonoacetate

Chemical Properties

Clear colorless liquid

Uses

tert-Butyl diethylphosphonoacetate is used as a reactant for preparation of hydroxymethylated dihydroxyvitamin D3 analogs via Wittig-Horner approach, as potential antitumor agents, synthesis of phosphopeptide mimetic prodrugs targeted to Src homology 2 (SH2) domain of signal transducer and activator of transcription 3 (Stat 3) and bicyclic triaminophosphine-promoted stereoselective synthesis of a,-unsaturated esters, fluorides, and nitriles from aldehydes and ketones using Wadsworth-Emmons phosphonates

Application

tert-Butyl diethylphosphonoacetate serves as an important intermediate in the synthesis of phosphonate derivatives, which are widely used in agrochemicals, pharmaceuticals, and materials science.

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Triethyl phosphite (485 g) is warmed up to 90°C under N2 atmosphere in a three-necked round-bottomed flask, and /-butyl bromoacetate (541 g) is added dropwise into the system within 2 h. Then, the mixture is stirred at 90°C for around 4 hours and cooled to room temperature. The obtained mixture is distilled under vacuo to remove compounds with low boiling points, and the residue is collected as a colorless liquid tert-butyl diethylphosphonoacetate in 97 percent yield (680 g).

References

[1] Chemistry - A European Journal, 1999, vol. 5, # 4, p. 1218 - 1225
[2] Tetrahedron, 2009, vol. 65, # 49, p. 10192 - 10213
[3] Patent: WO2015/101554, 2015, A1. Location in patent: Page/Page column 17
[4] Patent: US2015/183764, 2015, A1. Location in patent: Paragraph 0039
[5] Journal of the American Chemical Society, 2007, vol. 129, # 47, p. 14818 - 14825