Sodium hydride → (2,4-Difluoro-5-nitrophenyl) 1-pyrrolidinecarboxylate

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Reaction Steps

To a stirred, cold (0° C.) mixture of 1.74 g of sodium hydride (0.072 mole, 2.9 g of a 60% oil suspension) and 7.0 g (0.039 mole) of 2,4-difluoro-5-nitrophenol in 100 mL of tetrahydrofuran was added 6.4 g (0.048 mole) of 1-pyrrolidinecarbonyl chloride. The reaction mixture was allowed to warm to room temperature and was stirred for four hours. The mixture was diluted with ethyl acetate and was washed with an aqueous 10% hydrochloric acid solution. The organic phase was dried over anhydrous magnesium sulfate, filtered and filtrate evaporated under reduced pressure leaving a semi-solid residue. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate:n-heptane (50:50) to yield 7.2 g of (2,4-difluoro-5-nitrophenyl) 1-pyrrolidinecarboxylate. The nmr and ir spectra were consistent with the proposed structure.

Provenance & Evidence