Non-defluorinative electrochemical silylation of ethyl trifluoroacetate: A practical synthesis of trifluoroacetyltrimethylsilane via its ethyltrimethylsilyl ketal
An efficient method for the preparation of original trifluoroacetyltrimethylsilane, CF3COSiMe3 (3), in two steps from readily available ethyl trifluoroacetate is described. Electrochemical reduction of this ester using a sacrificial anode and performed on a semimolar scale afforded the unprecedented corresponding ketal, CF3C(SiMe3)(OSiMe3)OEt (2) in 30-56% isolated yield. Treated with concentrated sulphuric acid at room temperature, the latter directly led to pure acylsilane 3 in 86% yield.
Bordeau, Michel,Clavel, Philipe,Barba, Alic,Berlande, Muriel,Biran, Claude,Roques, Nicolas
Defluorination-silylation of alkyl trifluoroacetates to 2,2-difluoro-2-(trimethylsilyl)acetates by copper-deposited magnesium and trimethylsilyl chloride
Reductive defluorination-silylation of alkyl trifluoroacetates with copper-deposited magnesium and trimethylsilyl chloride (TMS-Cl) gave 2,2-difluoro-2-(trimethylsilyl)acetates, potential difluoromethylene building blocks, in 60-68% yields.
Utsumi, Shinya,Katagiri, Toshimasa,Uneyama, Kenji
experimental part
p. 580 - 583
(2012/01/14)
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