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Synthesis of malondialdehyde-1-2H and malondialdehyde-1,3-2H2

✍ Scribed by Ashis K. Basu; Lawrence J. Marnett

Publisher
John Wiley and Sons
Year
1985
Tongue
French
Weight
215 KB
Volume
22
Category
Article
ISSN
0022-2135

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✦ Synopsis

Two synthetic routes for deuterium labelling of 1,1,3,3-tetraethoxypropane, the precursor of the ubiquitous natural compound malondialdehyde, are described. In one scheme, deuterium is inc.orporated in ethyl vin 1 ether by metalation ing with $,,,. The conversion of the deuterated ether to monodeuterated tetraethoxypropane, however, proceeds with an overall yield of only -5%. As an alternative route, we have metalated the bis-1.3-propylene dithioacetal of malondialdehyde which deuterium incorporation (92%).

In addition, the latter method allows isotopic labelling of either one or two deuterium(s)/molecule. Hydrolysis of the deuterated dithioacetal to the corresponding tetraethoxypropane can be best effected by refluxing with HgO(red)/HgC12/BF3-etherate in the presence of CH(OC2H5)3/C2H50H. The overall yield of the method is 18%.

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