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Synthesis of [1,2,3,4,5‐ 13 C 5 ] palmitic acid
Author(s) -
Yuan SunShine,
Ajami Alfred M.
Publication year - 1984
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.2580210606
Subject(s) - chemistry , deoxygenation , saponification , yield (engineering) , palmitic acid , alkylation , catalysis , alcohol , carbonylation , organic chemistry , palladium , medicinal chemistry , nuclear chemistry , carbon monoxide , fatty acid , materials science , metallurgy
Abstract Carbonylation of 1‐undecene with 13 CO under a hydrogen atmosphere with palladium‐stannous chloride catalyst afforded [1‐13C]dodecanoic (lauric) acid on a 0.25 mole scale. Reduction to the alcohol and treatment with concentrated HBr gave 1‐[1‐ 13 C]bromododecane which was used to alkylate the Na + , Li + mixed diananion of ethyl acetoacetate selectively at the 4‐position in 73% yield. Reductive deoxygenation of the resulting 3‐oxo intermediate, followed by saponification and purification, gave [1,2,3,4,5‐ 14 C 5 ]hexadecanoic (palmitic) acid in 50% yield.