Preparation of no carrier added fluorine-18 labeled 16-fluorohexadecanoic and fluoroacetic acids from highly reactive tetraethylammonium [18F]fluoride

A. L. Bosch, T. R. Degrado, S. J. Gatley

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

No carrier added tetraethylammonium [18F]fluoride prepared via synthesis and hydrolysis of fluorotrimethylsilane was reacted with methyl 16-iodohexadecanoate in acetonitrile. At 80°C, yields of up to 80% were found with reaction times of 20-30 min. As would be expected for fluoride-for-iodide exchange, reactions were slower than previously-reported cyclic sulfate and triflate displacements. TLC and reverse-phase HPLC indicated that a single pure radioactive product was formed, which was hydrolyzed with alkali to the free acid. NMR spectroscopy of a carrier added preparation was consistent with assignment as 16-fluorohexadecanoic acid and no rearrangement to the 15-fluoro compound. [18F]Fluoroacetic acid was prepared analogously in high yield from ethyl iodoacetate. The results are discussed in terms of guidelines for syntheses of other 18F compounds and of the properties of near anhydrous tetraethylammonium fluoride in acetonitrile.

Original languageEnglish (US)
Pages (from-to)305-308
Number of pages4
JournalInternational Journal of Radiation Applications and Instrumentation. Part
Volume37
Issue number4
DOIs
StatePublished - 1986

ASJC Scopus subject areas

  • Radiation
  • Engineering(all)

Fingerprint Dive into the research topics of 'Preparation of no carrier added fluorine-18 labeled 16-fluorohexadecanoic and fluoroacetic acids from highly reactive tetraethylammonium [<sup>18</sup>F]fluoride'. Together they form a unique fingerprint.

Cite this