Potassium Carbonate → HCID 66777315, compound

HRID 2091380Notes

Reaction equation

HRID 2091380 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:18])=[C:13]([C:15](=O)[CH3:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](=O)([O-])[O-].[K+].[K+].BrC[C:27](=[O:30])[CH2:28][CH3:29]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:18][C:16]([C:27](=[O:30])[CH2:28][CH3:29])=[C:15]([CH3:19])[C:13]=2[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131561-Bromo-2-butanoneHCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

Product 1

HCID 66777315HCID 66777315, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (150 mL) of 1-[5-(benzyloxy)-2-hydroxyphenyl]ethanone (7.8 g) synthesized in Example 82(1) in N,N-dimethylformamide were added potassium carbonate (13.2 g) and 1-bromobutan-2-one (5.0 mL) at room temperature, and the mixture was stirred at room temperature for 3 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 (100 mL) again, 1,8-diazabicyclo[5.4.0]undec-7-ene (4.9 mL) was added to the solution, and the mixture was stirred at 110° C. with heating for 1 hr. After cooling to room temperature, the reaction mixture was quenched with 1N hydrochloric acid, and the 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 (6.2 g, 66%) as a colorless solid.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through celite
  3. additionWater was added to the filtrate
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (100 mL) again
  9. addition1,8-diazabicyclo[5.4.0]undec-7-ene (4.9 mL) was added to the solution
  10. stirringthe mixture was stirred at 110° C.
  11. temperaturewith heating for 1 hr
  12. temperatureAfter cooling to room temperature
  13. customthe reaction mixture was quenched with 1N hydrochloric acid
  14. extractionthe mixture was extracted with diethyl ether
  15. concentrationThe extract was concentrated under reduced pressure
  16. customthe precipitated compound was recrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-feb1dc5c2085462eb933b01265ab444d
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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