Hydrochloric Acid → (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol

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Reaction Steps

[(1R)-1-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]ethyl]3,5-dinitrobenzoate (50 g) was dissolved in methanol (2 liters). To the solution was added dropwise 1N sodium hydroxide aqueous solution (255 ml) at room temperature. The mixture was stirred for an hour at room temperature and neutralized with 1N hydrochloric acid (127 ml). Methanol was distilled off under reduced pressure. To the residue were added ethyl acetate (1 liter) and water (200 ml). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline (200 ml), dried over magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1:3) to give (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (25 g) as a pale yellow oily substance.

Provenance & Evidence