Reaktion #69515

Reaktionsgleichung

{[(3,3-difluorocyclobutyl)methoxy]methyl}benzene

iodotrimethylsilane

triethylamine

methanesulfonyl chloride

sodium hydrogencarbonate

→

title compound

Ausbeute 92.8%

(3,3-Difluorobutyl)methyl methanesulfonate

Ausbeute 92.8%

Lösungsmittel

dichloromethane

n-heptane ethyl acetate

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at room temperature for one hour
2. 2
   workup.ADDITIONThe reaction mixture was poured into ice-
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   workup.ADDITIONTo the reaction mixture, were added ice and sodium thiosulfate
6. 6
   Extraktionextracted with dichloromethane
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   FiltrationThe mixture was filtered
9. 9
   workup.DISTILLATIONthe solvent in the filtrate was distilled off under reduced pressure
10. 10
    workup.DISSOLUTIONthe resultant crude product was dissolved in dichloromethane (100 mL)
11. 11
    workup.STIRRINGwhile stirring on ice
12. 12
    workup.STIRRINGstirred at room temperature over one day and night
13. 13
    workup.STIRRINGAfter thoroughly shaking the mixture
14. 14
    Sonstigethe organic layer was then separated
15. 15
    Waschenthe organic layer was washed with brine
16. 16
    Trocknendried over anhydrous magnesium sulfate
17. 17
    FiltrationThe mixture was filtered
18. 18
    workup.DISTILLATIONthe solvent in the filtrate was distilled off under reduced pressure
19. 19
    SonstigeThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

Vorschrift

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).

Quelle