Hydrogen Peroxide → HCID 14722413, compound

HRID 1031687Notes

Reaction equation

HRID 1031687 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:3]=1[C:20]([CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1)=[O:21].[OH-].[Na+].OO.C(OCC)(=[O:40])C>CO.O>[OH:40][C:22]1[C:20](=[O:21])[C:3]2[CH:4]=[C:5]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:7][C:2]=2[O:1][C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 54366716HCID 54366716, compound

Product 1

HCID 14722413HCID 14722413, compoundYield 10.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2.0 g of 2-(3,4-dimethoxyphenyl)vinyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone was suspended in 20 ml of methanol. Thereto was added 3.7 ml of a 15% aqueous sodium hydroxide solution to obtain a solution. Thereto was dropwise added 2.5 ml of a 15% aqueous hydrogen peroxide solution in 10 minutes at 0°-5° C. The mixture was stirred for 10 hours at the same temperature. The reaction mixture was introduced into a mixture of 50 ml of ethyl acetate and 50 ml of water. The organic layer was separated, washed with water, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: a 200 : 1 mixture of chloroform and methanol) to obtain 220 mg (yield: 10.7%) of 3-hydroxy-7-methylsulfonylamino-2-(3,4-dimethoxyphenyl)-6-phenoxy-4H-1-benzopyran-4-one.

Workup

  1. customto obtain a solution
  2. customin 10 minutes
  3. customat 0°-5° C
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by a column chromatography (eluant
  9. additiona 200 : 1 mixture of chloroform and methanol)

Sources & evidence

ORD record
ord-727818754a5b427ea4d66a2a8b2a3f51
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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