Triethylamine → HCID 86652473, compound

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).

1. stirringstirred at room temperature for one hour
2. additionThe reaction mixture was poured into ice-
3. extractionextracted with ethyl acetate
4. dry with materialdried over anhydrous magnesium sulfate
5. additionTo the reaction mixture, were added ice and sodium thiosulfate
6. extractionextracted with dichloromethane
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationThe mixture was filtered
9. distillationthe solvent in the filtrate was distilled off under reduced pressure
10. dissolutionthe resultant crude product was dissolved in dichloromethane (100 mL)
11. stirringwhile stirring on ice
12. stirringstirred at room temperature over one day and night
13. stirringAfter thoroughly shaking the mixture
14. customthe organic layer was then separated
15. washthe organic layer was washed with brine
16. dry with materialdried over anhydrous magnesium sulfate
17. filtrationThe mixture was filtered
18. distillationthe solvent in the filtrate was distilled off under reduced pressure
19. customThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

ORD record

ord-9564b3ef1b9a4af4baa8063800261088

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530504B2