m-Chloroperbenzoic acid → 3-(3,4-Dichlorophenyl)-3,4-epoxy-1-butanol t-butyldimethylsilyl ether

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Reaction Steps

3.00 g (9.05 mmole) of 3-(3,4-dichlorophenyl)-3-butenol t-butyldimethylsilyl ether [prepared as described in Example 1(b)] were dissolved in 60 ml of methylene chloride, and 2.52 g (30.0 mmole) of sodium hydrogencarbonate and 3.88 g (15.7 mmole) of 3-chloroperbenzoic acid (content: 70%) were added to the resulting solution. The mixture was then stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was diluted with methylene chloride and then washed with a 1 N aqueous solution of sodium hydroxide and with a saturated aqueous solution of sodium chloride. The organic layer was then dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reduced pressure. The resulting residue was then purified by silica gel column chromatography, using a gradient elution method, with mixtures of hexane and diethyl ether ranging from 24:1 to 19:1 by volume as the eluent, to obtain 2.70 g of the title compound.

Provenance & Evidence