反应 #103162
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openreactiondata ↗doi:10.6084/m9.figshare.5104873.v1; patent:US08530504B2
反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: To a dichloromethane (16.6 mL) solution of {[(3,3-difluorocyclobutyl)methoxy]methyl}benzene (2.40 g, 11.3 mmol), was added dropwise iodotrimethylsilane (2.46 mL, 16.9 mmol) while stirring on ice, and stirred at room temperature for one hour. The reaction mixture was poured into ice-cooled aqueous sodium hydrogencarbonate, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. To the reaction mixture, were added ice and sodium thiosulfate, extracted with dichloromethane, and dried over anhydrous magnesium sulfate. The mixture was filtered, then the solvent in the filtrate was distilled off under reduced pressure, and the resultant crude product was dissolved in dichloromethane (100 mL), triethylamine (2.02 mL, 14.4 mmol) and methanesulfonyl chloride (1.31 mL, 14.5 mmol) were added while stirring on ice, and stirred at room temperature over one day and night. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was then separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate:n-heptane/ethyl acetate=11/4) to obtain the title compound (2.10 g, 10.49 mmol). stirred at room temperature for one hour The reaction mixture was poured into ice- extracted with ethyl acetate dried over anhydrous magnesium sulfate To the reaction mixture, were added ice and sodium thiosulfate extracted with dichloromethane dried over anhydrous magnesium sulfate The mixture was filtered the solvent in the filtrate was distilled off under reduced pressure the resultant crude product was dissolved in dichloromethane (100 mL) while stirring on ice stirred at room temperature over one day and night After thoroughly shaking the mixture the organic layer was then separated the organic layer was washed with brine dried over anhydrous magnesium sulfate The mixture was filtered the solvent in the filtrate was distilled off under reduced pressure The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate
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