Sodium hydride → Diethyl 2-fluoro-2-phenylmalonate

Beteiligte Stoffe

Reaktionsschritte

Diethyl phenylmalonate (708 mg, 650 μL, 3 mmole) was dissolved in anhydrous tetrahydrofuran (5 mL) under nitrogen. Sodium hydride (144 mg as a 60% oil dispersion, 3.6 mmole) was added and the mixture was stirred until hydrogen evolution ceased (about 15 minutes). The solution was then diluted with anhydrous toluene (10 mL) and added dropwise to a solution of N-fluoro-N-neopentyl-n-butylsulfonamide (675 mg, 3 mmole) in anhydrous toluene (5 mL) and the mixture was stirred at room temperature under nitrogen. After 30 minutes the reaction mixture was diluted with ether (100 mL), washed with aqueous 1N oxalic acid (30 mL), 10% aqueous potassium bicarbonate (30 mL), and saturated aqueous sodium chloride (30 mL) solutions, and then dried over anhydrous magnesium sulfate. Filtration, removal of solvent under reduced pressure, and purification by flash column chromatography (silica, 1:1 methylene chloride-hexane) yielded diethyl 2-fluoro-2-phenylmalonate as a colorless liquid (508 mg). 1H NMR was consistent with the desired structure.

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