Water → HCID 66777216, compound

HRID 2091349Notes

Reaction equation

HRID 2091349 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(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:18][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:15]([CH3:16])[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 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

Product 1

HCID 66777216HCID 66777216, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (200 mL) of 1-[5-(benzyloxy)-2-hydroxyphenyl]ethanone (15.3 g) synthesized in Example A82(1) in N,N-dimethylformamide were added potassium carbonate (13.1 g) and ethyl bromoacetate (7.7 mL) at room temperature, and the mixture was stirred at room temperature 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, the obtained residue was dissolved in N,N-dimethylformamide (100 mL) again, and 1,8-diazabicyclo[5.4.0]undec-7-ene (12.2 mL) was added to the solution. The reaction mixture was stirred at 80° C. overnight. 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 (3.3 g, 17%) 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 (100 mL) again
  4. addition1,8-diazabicyclo[5.4.0]undec-7-ene (12.2 mL) was added to the solution
  5. stirringThe reaction mixture was stirred at 80° C. overnight
  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-2144a668a9d940a783044bbd8f91030f
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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