Potassium Carbonate → HCID 66777538, compound

1-[2-Hydroxy-5-(2-methoxyethoxy)phenyl]ethanone (7.0 g) synthesized in the above-mentioned (1) was dissolved in N,N-dimethylformamide (140 mL). Potassium carbonate (13.8 g) and 2-bromo-1-cyclohexylethanone (8.9 g) synthesized in Example A51(1) were added to the reaction mixture at room temperature, and the mixture was stirred for 15 hr. The reaction mixture was filtered through celite, water (200 mL) was added, and the mixture was extracted with diethyl ether (100 mL×2). The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide solution (100 mL), DBU (5.3 mL) was added at room temperature, and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was allowed to cool to room temperature, 1N hydrochloric acid (100 mL) was added, and the mixture was extracted with diethyl ether (100 mL×2). The extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20, volume ratio) to give the title object compound (10.3 g, 98%) as a pale-yellow oil.

1. additionwere added to the reaction mixture at room temperature
2. filtrationThe reaction mixture was filtered through celite, water (200 mL)
3. additionwas added
4. extractionthe mixture was extracted with diethyl ether (100 mL×2)
5. washThe extract was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. dissolutionThe residue was dissolved in N,N-dimethylformamide solution (100 mL)
9. additionDBU (5.3 mL) was added at room temperature
10. stirringthe mixture was stirred at 100° C. for 1 hr
11. addition1N hydrochloric acid (100 mL) was added
12. extractionthe mixture was extracted with diethyl ether (100 mL×2)
13. washThe extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
14. dry with materialdried over magnesium sulfate
15. concentrationconcentrated under reduced pressure
16. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20, volume ratio)

ORD record

ord-453c6fa54458495797c0fe0aadc07abe

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2