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

✍ Scribed by Michael J. Bienkowski; Melissa A. Tuttle; Lawrence J. Marnett

Publisher
John Wiley and Sons
Year
1980
Tongue
French
Weight
234 KB
Volume
17
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of 1,1,3,3‐tetraethoxypropane‐1,2,3‐^14^C~3~ 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‐^14^C~3~(1,3 propanedial‐1,2,3‐^14^C~3~) which is isolated and stored as the sodium salt. One of the intermediates in the synthesis of tetraethoxypropane is ethyl vinyl‐[1,2‐^14^C~2~] 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 [^14^C] labeled compounds.

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