clear colorless to light yellow liquid
Trimethyl phosphonoacetate is used in the preparation of sarin A by intramolecular Mannich-type reactions. It is involved in the Horner-Wadsworth-Emmons olefination with aldehydes and ketones to give acrylic esters. It is also involved in oxa-Michael reactions, prenylation of oxindoles and heterocyclization reactions.
Trimethyl phosphonoacetate is an important Wittig-horner reagent, which can be used to manufacture important intermediates of natural compounds such as vitamins, drugs, insect pheromones, etc.
Reactant involved in:
Intramolecular Mannich-type reactions to produce the sarain A diazatricyclic core
Organocatalytic oxa-Michael reactions
Prenylation and geranylation of oxindoles
Intramolecular Horner-Wadsworth-Emmons reactions
Olefin cross-metathesis / heterocyclization
ChEBI: Trimethyl phosphonoacetate is a phosphonic ester.
reaction type: C-C Bond Formation
The trimethyl phosphonoacetate is prepared from trimethyl phosphite and methyl chloroacetate through Michael Arbuzov rearrangement reaction. The synthetic method satisfies the chemical equations that CH2ClCOOH + CH3OH → CH5ClO2 + H2O, CH5ClO2 + C3H9O3P → C5H11O5P + CH3Cl.
