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
✍ Scribed by C.H. Lam; M.S.F. Lie Ken Jie
- Publisher
- Elsevier Science
- Year
- 1976
- Tongue
- English
- Weight
- 522 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0009-3084
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✦ Synopsis
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)-methoxyoctadecanoates and the 2,6-disub stituted tetrahydropyranyl derivative, methyl 6,10-epoxyoctadecanoate.