Preparation of methyl cis-9,cis-12-octadecadienoate-16,16,17,17-d4 |
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Authors: | RO Adlof EA Emken |
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Abstract: | An eight-step synthesis is described which gives an overall yield of ~30% methyl cis-9,cis-12-octadecadienoate-16,16,17,17-d4. 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 1-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 spectrometry (MS) indicated 96%-d4. |
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Keywords: | deuterium linoleic |
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