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Microsynthesis of 3H-sterculic acid with high specific activity

✍ Scribed by H. van Tilborg

Publisher
John Wiley and Sons
Year
1975
Tongue
French
Weight
139 KB
Volume
11
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Copper‐catalysed addition of ethyl diazoacetate to methyl scearolate (20 mmol scale) and subsequent saponification gave 9, 10‐carboxymethylene, 9‐octadecenoic acid in 67% yield. The letter was decarbonylated by treatment with HClO~4~/Ac~2~O in the cold (76 μmol scale) to give cyclopropenium perchlorate, which was reduced with NaBH^4^. After removal of non‐acidic by‐products. sterculic acid labelled with ^3^H in the cyclopropene ring was obtained in 9% yield. Its specific activity was 140 mCi/mmol, the radiochemical purity was 90%.

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