Fatty acids, part 5: A study of the oxymercuration-demercuration reaction of some C11-unsaturated fatty esters and methyl octadec-cis-10-en-5-ynoate

Add time:07/19/2019    Source:sciencedirect.com

The methoxymercuration-demercuration reactions of all the methyl cis-undecenoates are reported. Oxymercuration reaction of acetylenic esters gives keto- and hydroxy-esters when demercurated with hydrochloric acid and sodium borohydride respectively. Similar reactions are carried out with methyl octadec-cis-10-en-5-ynoate, which give the methyl 5(6)-oxooctadec-cis-10-enoate and 5(6)-hydroxy-10(11)-methoxyoctadecanoate isomers.Reduction of the methyl 5(6)-oxooctadec-cis-10-enoates with sodium borohydride yields the corresponding methyl hydroxy-esters, which on treatment with mercuric acetate (in methanol) and demercurated with sodium borohydride give methyl 5-hydroxy-10(11)-methoxyocta-decanoates and the 2,6-disubstituted tetrahydropyranyl derivative, methyl 6,10-epoxyoctadecanoate.

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