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Preparation of methyl cis-9,cis-12-octadecadienoate-16,16,17,17-d4

✍ Scribed by R.O. Adlof; E.A. Emken

Publisher: Elsevier Science
Year: 1981
Tongue: English
Weight: 357 KB
Volume: 29
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(81)90043-8

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✦ Synopsis

An eight-step synthesis is described which gives an overall yield of ~30% methyl cis-9,cis-12-octadecadienoate-16,16,17,17-d 4. The preparation utilizes easily obtainable starting materials. Tris(triphenylphosphine)chlororhodium (I) catalyst is used for incorporation of the deuterium isotopes. The double bond in the 9 position is created by the Wittig coupling of I-non-3-enyl-d4-triphenylphosphonium bromide to methyl 8-formyloctanoate. Various methods for preparation of the intermediate and final products are discussed. Partial argentation resin chromatography was used to remove the ~9% trans/cis, cis/trans, and trans/trans isomers also produced. Analysis of the final product by mass spectTometry (MS) indicated 96%-d 4.

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