A convenient and inexpensive synthesis of labelled methylmalonic and propionic acids: Application to the synthesis of methyl-d3-malonic and of propionic-3,3,3-d3 acids

Article abstract of DOI:10.1002/(SICI)1099-1344(199911)42:11<1085::AID-JLCR264>3.0.CO;2-4

A synthetic route for obtaining highly pure methylmalonic and propionic acids labelled at the methyl groups is validated by the preparation of methyl-d₃-malonic and propionic-3,3,3-d₃ acids. The synthesis involves the alkylation of the diethyl allylmalonate with iodomethane-d₃, deallylation of the resulting diethyl allylmethyl-d₃-malonate by treatment with (η²-propene)Ti(O-i-Pr)₂ and hydrolysis. Decarboxylation of the obtained methyl-d₃-malonic acid affords propionic-3,3,3-d₃ acid.