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Synthesis of [ 13 C 5 ] and [carbonyl‐ 14 C]‐5‐chlorofuran‐2‐carboxylic acid
Author(s) -
Dorff Peter N.,
Powell Mark E.,
Elmore Charles S.
Publication year - 2011
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.1829
Subject(s) - chemistry , furan , carboxylation , carboxylic acid , yield (engineering) , lithium (medication) , organic chemistry , catalysis , medicine , materials science , metallurgy , endocrinology
The inventory of labeled compounds and methods for their preparation are constantly growing, but still more building blocks of biologically relevant compounds need to be developed. Furans are frequently encountered in bioactive molecules, and a good synthesis of labeled furan is found in the literature. We required a relatively uncommon labeled furan, 5‐chloro‐2‐furoic acid, for investigative work labeled with C‐13 and C‐14. Carboxylation of the lithium anion of [ 13 C 4 ]furan with 13 CO 2 followed by chlorination using benzyltrimethylammonium dichloroiodate provided the target compound in modest yield and high purity. The same procedure was then repeated with unlabeled furan and 14 CO 2 to give [carbonyl‐ 14 C]‐5‐chlorofuran‐2‐carboxylic acid. Copyright © 2010 John Wiley & Sons, Ltd.