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A new simple synthesis of 1,3-dideuterated malondialdehyde (3-hydroxy[1,3-2H2]-2-propenal)

✍ Scribed by Pietro Allevi; Mario Anastasia; Pierangela Ciuffreda

Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
308 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A synthetic route for obtaining 1‐butoxy‐1,3,3‐triethoxy[1,3‐^2^H~2~]propane a stable diacetal of the malondialdehyde, is described. The synthesis involves the condensation of deuterated butylvinyl 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 ^2^H~2~O. From the diacetal the 1,3‐dideuterated malondialdehyde was obtained by a short treatment with acid ion exchange resin.

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