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Microsynthesis of 3 H‐sterculic acid with high specific activity
Author(s) -
van Tilborg H.
Publication year - 1975
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590110214
Subject(s) - saponification , yield (engineering) , chemistry , perchlorate , cyclopropene , ethyl diazoacetate , medicinal chemistry , ring (chemistry) , nuclear chemistry , organic chemistry , cyclopropanation , catalysis , ion , materials science , metallurgy
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%.