Dimethylformamide → 6'-Hydroxy-2'-methoxycarbonylmethoxy-4-methyldihydrochalcone

HRID 230871Notes

Reaction equation

HRID 230871 reaction equation
C([O:8][C:9]1[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[C:10]=1[C:11](=[O:21])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)C1C=CC=CC=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][CH3:43])=[O:41]>CC(C)=O.O>[OH:8][C:9]1[C:10]([C:11](=[O:21])[CH:12]=[CH:13][CH:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH2:19]2)=[C:22]([O:26][CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 671363262'-Benzyloxy-6'-hydroxy-4-methylchalcone

Product 1

HCID 671360496'-Hydroxy-2'-methoxycarbonylmethoxy-4-methyldihydrochalcone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 2′-benzyloxy-6′-hydroxy-4-methylchalcone (0.69 g) in acetone (10 mL)-N,N-dimethylformamide (10 mL) were added potassium carbonate (0.41 g) and methyl bromoacetate (0.21 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (10 mL). To the solution was added 10% palladium-carbon powder (0.29 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 5 hours. Dichloromethane was added to the mixture, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound (0.58 g).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (10 mL)
  6. additionTo the solution was added 10% palladium-carbon powder (0.29 g)
  7. stirringthe mixture was stirred at room temperature under a hydrogen atmosphere for 5 hours
  8. additionDichloromethane was added to the mixture
  9. customthe insoluble material was removed by filtration
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cac804399ff54536b08c6cc891e72c49
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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