Synthesis of methyl ω-deuterated tetradecanoate and hexadecanoate

Add time:08/24/2019    Source:sciencedirect.com

Methyl ω-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 iodo 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 ω-deuterated derivatives of methyl hexadecanoate may be prepared by the same methods from methyl hydrogen hexadecanedioate. The two methods should be generally applicable in the synthesis of ω-deuterated alkanoic acids.

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