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Synthese de l'acide nervonique 14C-24 (acide cis-tétracosène-15 oïque 14C-24)

✍ Scribed by T. Moriya; M. Pabiot; L. Pichat


Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
348 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

Methyl iodide‐^14^C was condensed with 2‐(1‐lithio‐hept‐1‐yn‐6‐yl) 1,3‐dioxolanne 4 in presence of HMPT and benzene to give 2‐(oct‐2‐yn‐8‐yl‐1‐^14^C) 1,3‐dioxolanne 5.

Catalytic reduction of 5, followed by acid hydrolysis led to pelargonic aldehyde 9‐^14^C 7. Condensation of this aldehyde 7 with an excess of w‐carbomethoxy‐tetradecylidene), triphenyl phosphorane 11 produced methyl nervonate 24‐ ^14^C 12. The latter was isolated from its trans isomer by chromatography on a silver nitrate impregnated silicagel column. Finally, nervonic acid 24‐^14^C 13 was obtained by alkaline hydrolysis (specific activity : 52 mCi/mMole) with an overall yield of 7% based on methyl iodide‐^14^C.


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