Water → HCID 43332515, compound

HRID 2091359Notes

Reaction equation

HRID 2091359 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+].Br[CH2:26][C:27](=[O:29])C.O>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:29])[CH3:26])=[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

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

Product 1

HCID 43332515HCID 43332515, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution (120 mL) of 1-[5-(benzyloxy)-2-hydroxyphenyl]ethanone (6.4 g) synthesized in Example A82(1) in N,N-dimethylformamide were added potassium carbonate (10.8 g) and bromoacetone (4.8 g) at room temperature, and the mixture was stirred at 80° C. for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was concentrated under reduced pressure, and the obtained residue was dissolved in N,N-dimethylformamide (120 mL) again, and 1,8-diazabicyclo[5.4.0]undec-7-ene (5.1 mL) was added to the solution. The reaction mixture was stirred at 80° C. for 2 hr. After cooling to room temperature, water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was concentrated under reduced pressure, and the obtained solid was washed with ethanol-isopropyl ether to give the title object compound (2.5 g, 34%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. concentrationThe extract was concentrated under reduced pressure
  3. dissolutionthe obtained residue was dissolved in N,N-dimethylformamide (120 mL) again
  4. addition1,8-diazabicyclo[5.4.0]undec-7-ene (5.1 mL) was added to the solution
  5. stirringThe reaction mixture was stirred at 80° C. for 2 hr
  6. temperatureAfter cooling to room temperature
  7. additionwater was added to the reaction mixture
  8. extractionthe mixture was extracted with diethyl ether
  9. concentrationThe extract was concentrated under reduced pressure
  10. washthe obtained solid was washed with ethanol-isopropyl ether

Sources & evidence

ORD record
ord-59a1a6151bfe417e8bb84c12015fb762
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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