Potassium Carbonate → Cyclohexyl(5,7-difluoro-3-methyl-1-benzofuran-2-yl)methanone

To a solution (50 mL) of 1-(3,5-difluoro-2-hydroxyphenyl)ethanone (2.8 g) in N,N-dimethylformamide were added potassium carbonate (6.7 g) and 2-bromo-1-cyclohexylethanone (4.0 g) synthesized in Example A51(1) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was allowed to cool to room temperature, and filtered through celite. Water was added to the filtrate, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in N,N-dimethylformamide (50 mL) again, 1,8-diazabicyclo[5.4.0]undec-7-ene (2.6 mL) was added to the solution, and the mixture was stirred at 110° C. 1 hr with heating. After cooling to room temperature, the reaction mixture was quenched with 1N hydrochloric acid, and the reaction mixture was extracted with diethyl ether. The extract was concentrated under reduced pressure, and the precipitated compound was recrystallized from diisopropyl ether-hexane to give the title object compound (3.1 g, 70%) as a colorless solid.

1. customsynthesized in Example A51(1) at room temperature
2. temperatureto cool to room temperature
3. filtrationfiltered through celite
4. additionWater was added to the filtrate
5. extractionthe mixture was extracted with diethyl ether
6. washThe extract was washed with saturated brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (50 mL) again
10. addition1,8-diazabicyclo[5.4.0]undec-7-ene (2.6 mL) was added to the solution
11. stirringthe mixture was stirred at 110° C
12. temperature1 hr with heating
13. temperatureAfter cooling to room temperature
14. customthe reaction mixture was quenched with 1N hydrochloric acid
15. extractionthe reaction mixture was extracted with diethyl ether
16. concentrationThe extract was concentrated under reduced pressure
17. customthe precipitated compound was recrystallized from diisopropyl ether-hexane

ORDレコード

ord-de1b53984aef4346b5818bd559f4abc8

出典データセット

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08436043B2