2-Bromoethanol → HCID 19358638, compound

HRID 377354Notes

Reaction equation

HRID 377354 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[O:9]2)=[C:4]([O:23][CH3:24])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][OH:34]>CN(C)C=O>[OH:34][CH2:33][CH2:32][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[O:9]2)=[C:4]([O:23][CH3:24])[CH:3]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 13964544HCID 13964544, compound

Product 1

HCID 19358638HCID 19358638, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-hydroxy-3',4',5-trimethoxy flavone (200 mg, 0.61 mmol) was dissolved in dimethylformamide and hereto was added potassium carbonate (253 mg, 3 equivalents) and 2-bromoethanol (65 μl, 1.5 equivalents). After the reaction mixture was refluxed for 3~4 hours, the solvent was removed under reduced pressure and the residue was diluted with chloroform and washed with water. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure and the residue was column-chromatograped to give 125 mg of the product (55%).

Workup

  1. temperatureAfter the reaction mixture was refluxed for 3~4 hours
  2. customthe solvent was removed under reduced pressure
  3. additionthe residue was diluted with chloroform
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1decc476487d448c822538482bd0ab0b
Source dataset
uspto-grants-2000_02
Patent number
US06025387

Reaction notes

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