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One-step reductive etherification of 4-[18F]fluoro-benzaldehyde with decaborane

✍ Scribed by Uta Funke; Hongmei Jia; Steffen Fischer; Matthias Scheunemann; Jörg Steinbach

Publisher: John Wiley and Sons
Year: 2006
Tongue: French
Weight: 165 KB
Volume: 49
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.1087

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✦ Synopsis

Reductive coupling reactions between 4-[ 18 F]fluoro-benzaldehyde ([ 18 F]1) and different alcohols by use of decaborane (B 10 H 14 ) as reducing agent have the potential to synthesize 4-[ 18 F]fluoro-benzylethers in one step. [ 18 F]1 was synthesized from 4trimethylammonium benzaldehyde (triflate salt) via a standard fluorination procedure (K[ 18 F]F/Kryptofix 1 222) in dimethylformamide at 908C for 25 min and purified by solid-phase extraction. Subsequently, reductive etherifications of [ 18 F]1 were performed as one-step reactions with primary and secondary alcohols, mediated by B 10 H 14 in acetonitrile at 608C. Various 4-[ 18 F]fluorobenzyl ethers (6 examples are shown) were obtained within 1-2 h reaction time in decay-corrected radiochemical yields of 12-45%.

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## Abstract A facile procedure for preparing 4‐fluoroantipyrine is reported. Treatment of antipyrine with molecular fluorine gives 4‐fluoroantipyrine (3) and 4,4‐difluoro‐3‐hydroxy‐2,3‐dimethyl‐1‐phenylpyrazolidin‐5‐one (2). The product distribution depends on the ratio of antipyrine and molecular