Hydrogen Peroxide → HCID 22037365, compound

HRID 861034Notes

Reaction equation

HRID 861034 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[C:9]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[C:10](=[O:12])[CH3:11].[OH:19]O.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[O:19][C:9]1([C:13]1[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=1)[C:10](=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 54245555HCID 54245555, compound

Product 1

HCID 22037365HCID 22037365, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(2-methylphenyl)-3-(4-pyridyl)-3-butene-2-one (step 1) (1.0 g, 4.2 mmol) in methyl alcohol (18 ml), a solution of H2O2 (30% by wt.) (0.95 g, 8.4 mmol) and sodium hydroxide (0.18 g 4.6 mmol) in water (4 ml) was added. The reaction was stirred at room temperature for 70 hours. After methyl alcohol was removed, water (25 ml) and ethyl acetate (100 ml) were added and the two phase mixture was stirred for 30 minutes. The layers were separated, and the aqueous layer was washed with ethyl acetate (100 ml). The combined organic layer was dried with Na2SO4, filtered and concentrated to give an oil. 4-(2-Methylphenyl)-3-(4-pyridyl)-3,4-epoxy-2-butanone was isolated from the oil residue by chromatography.

Workup

  1. customAfter methyl alcohol was removed
  2. additionwater (25 ml) and ethyl acetate (100 ml) were added
  3. stirringthe two phase mixture was stirred for 30 minutes
  4. customThe layers were separated
  5. washthe aqueous layer was washed with ethyl acetate (100 ml)
  6. dry with materialThe combined organic layer was dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oil

Sources & evidence

ORD record
ord-b7212178dfbe4691b0ae04d65ab75d0a
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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