A NEW SIMPLE SYNTHESIS OF 1,3-DIDEUTERATED MALONDIALDEHYDE (3-HYDROXY[1,3-(H-2)-2]-2-PROPENAL)

A synthetic route for obtaining 1-butoxy-1,3,3-triethoxy[1,3-H-2(2)]propane a stable diacetal of the malondialdehyde, is described. The synthesis involves the condensation of deuterated butyl vinyl ether with deuterated triethyl orthoformate in the presence of montmorillonite clay K-10. The deuteration of butyl vinyl ether was accomplished via the intermediary formation of a stannane derivative which was quantitatively metallated by n-butyllithium and then treated with (H2O)-H-2. From the diacetal the 1,3-dideuterated malondialdehyde was obtained by a short treatment with acid ion exchange resin.