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Synthese de l'acide nervonique 14 C‐24 (acide cis‐tétracosène‐15 oïque 14 C‐24)
Author(s) -
Moriya T.,
Pabiot M.,
Pichat L.
Publication year - 1981
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580180706
Subject(s) - chemistry , phosphorane , iodide , hydrolysis , aldehyde , methyl iodide , medicinal chemistry , column chromatography , yield (engineering) , nitric acid , benzene , catalysis , nuclear chemistry , organic chemistry , materials science , metallurgy
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.