Synthesis of malondialdehyde‐1,2,3‐14C3 via ethyl vinyl‐[1,2‐14C2] ether

作者：Michael J. Bienkowski, Melissa A. Tuttle, Lawrence J. Marnett · 发表于：Journal of Labelled Compounds and Radiopharmaceuticals · 年份：1980 · DOI：10.1002/jlcr.2580170502 · 被引用次数：4 · 研究领域：Fluorine in Organic Chemistry、Chemical Reactions and Isotopes、Analytical Chemistry and Chromatography

Abstract The synthesis of 1,1,3,3‐tetraethoxypropane‐1,2,3‐14C3 from uniformly labeled paraldehyde is described. The synthesis involves three steps and proceeds in an overall yield of 25%. The final product is greater than 95% radiochemically pure and it is stable indefinitely when stored as thoroughly degassed benzene solutions. Hydrolysis of radiolabeled tetraethoxypropane occurs in moderate yields to form malondialdehyde‐1,2,3‐14C3(1,3 propanedial‐1,2,3‐14C3) which is isolated and stored as the sodium salt. One of the intermediates in the synthesis of tetraethoxypropane is ethyl vinyl‐[1,2‐14C2] ether, which is isolable in 50% overall yield from paraldehyde. The widespread utilization of ethyl vinyl ether in organic synthesis suggests that the radiolabeled material should provide an entry to a large number of specifically [14C] labeled compounds.