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Synthesis of [1,2,3,4,5-13C5] palmitic acid

✍ Scribed by Sun-Shine Yuan; Alfred M. Ajami

Publisher
John Wiley and Sons
Year
1984
Tongue
French
Weight
303 KB
Volume
21
Category
Article
ISSN
0022-2135

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✦ Synopsis

Carbonylation of 1-undecene with 13C0 under a hydrogen atmosphere with pa 1 ladi um-s tannous ch 1 or ide cata 1 ys t afforded [ 1-13C Idodecanoi c ( 1 aur i c acid on a 0.25 mole scale. Reduction to the alcohol and treatment with concentrated HBr gave 1-[l-C]bromododecane which was used to alkylate the N a ' , Lit mixed diananion o f ethyl acetoacetate selectively at the 4-position in 73% yield.

Reductive deoxygenation of the resulting 3-0x0 intermediate, followed by saponification and purification, gave [ 1,2,3,4,5-14C5]hexadecanoic (palmi t ic 1 acid in 50% yield.

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