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Synthesis of methyl ω-deuterated tetradecanoate and hexadecanoate

✍ Scribed by P.W. Westerman; N. Ghrayeb

Publisher
Elsevier Science
Year
1981
Tongue
English
Weight
461 KB
Volume
29
Category
Article
ISSN
0009-3084

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✦ Synopsis

Methyl to-deuterated tetradecanoates have been prepared in high purity by two synthetic routes from methyl hydrogen tetradecanedioate. One method utilizes the selective reducing properties of sodium borodeuteride and sodium cyanoborodeuteride towards, acid chloride, ester, tosyloxy, and lode groups to introduce the deuterium label at only the carboxyl group of methyl hydrogen tetradecanedioate. The second procedure utilizes a coupling reaction between an organic halide and lithium di-(trideuteriomethyl) cuprate (I). Corresponding todeuterated derivatives of methyl hexadeeanoate may be prepared by the same methods from methyl hydrogen hexadecanedioate. The two methods should be generally applicable in the synthesis of to-deuterated alkanoie adds.

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