Sodium hydride → Diethyl 2-fluoro-2-phenylmalonate

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A solution of diethyl sodio(phenyl)malonate in anhydrous THF [prepared in conventional fashion by adding a 60% dispersion of NaH (0.64 mmol) in oil to PhCH(CO2Et)2 (0.15 g, 0.635 mmol) dissolved in THF (10 cm3)] was added dropwise to a cold (-10° C.) THF solution (15 cm3) of a 9:1 molar mixture (from the experiment described immediately above) of perfluoro-[N-fluoro-N-(4-pyridyl)methanesulfonamide] and its N-H precursor containing 0.20 g (0.63 mmol) of the N-F compound. The reaction mixture was allowed to warm to room temperature, then worked-up as described by R. E. Banks et al (J. Chem. Soc., Perkin Trans I, 1988 2805) for the product from the fluorination of diethyl sodio(phenyl)malonate with N-fluoroquinuclidinium fluoride, to provide diethyl fluoro(phenyl)malonate (0.15 g, 0.59 mmol, 93%) as a colourless oil [Found: C, 61.5; H, 6.2%; M (mass spec.) 254. Calc. for C13H15FO4 : C, 61.4; H, 5.9%; M, 254] with correct spectroscopic properties (i.r.; 1H and 19F n.m.r.).

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