Potassium Carbonate → HCID 66778746, compound

To a solution (10 mL) of 1-[2-hydroxy-5-(2-methoxyethoxy)phenyl]ethanone (0.55 g) synthesized in Example A79(1) in N,N-dimethylformamide were added potassium carbonate (1.1 g) and 1-bromo-3-methylbutan-2-one (0.56 g) synthesized in Example A75(1) 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 (10 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 (10 mL), and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.41 mL) was added to the solution at room temperature. The reaction mixture was stirred at 100° C. for 1 hr. The reaction mixture was allowed to cool to room temperature, 1N hydrochloric acid (10 mL) was added, and the mixture was extracted with diethyl ether (10 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=1:1, volume ratio) to give the title object compound (0.71 g, 98%) as a pale-yellow oil.

1. customsynthesized in Example A75(1) 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 (10 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 (10 mL)
9. addition1,8-diazabicyclo[5.4.0]undec-7-ene (0.41 mL) was added to the solution at room temperature
10. stirringThe reaction mixture was stirred at 100° C. for 1 hr
11. addition1N hydrochloric acid (10 mL) was added
12. extractionthe mixture was extracted with diethyl ether (10 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=1:1, volume ratio)

ORD record

ord-335ebc30918748b489ce77b176192ac4

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2