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Synthesis of di‐, tetra, and hexadeuterated 11‐octadecenoates
Author(s) -
Dejarlais W. J.,
Emken E. A.
Publication year - 1978
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580150151
Subject(s) - wittig reaction , chemistry , tetra , deuterium , alkyl , halide , organic chemistry , saturation (graph theory) , medicinal chemistry , physics , mathematics , quantum mechanics , combinatorics
Methyl esters of 11‐octadecenoic‐15, 16‐d 2 , −15, 15, 16, 16‐d 4 , and −10, 10, 15, 15, 16, 16‐d 6 acids were prepared by Wittig synthesis from intermediates derived from 11‐bromoundecanoic acid and 7‐chloro‐3‐heptyne. The dideuterated acid was prepared by partial hydrogenation of the heptyne followed by saturation with deuterium to 1‐chloroheptane‐4, 5‐d 2 for Wittig synthesis. Saturation of the heptyne with deuterium provided the Wittig intermediate for tetradeuterated acids. The hexadeuterated acids were prepared from tetradeuterated alkyl halide and 10‐formyldecanoate‐10, 10‐d 2 .