Triethylamine → HCID 86652473, compound

Participants

Reaction Steps

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).

Provenance & Evidence