Hydrogen Peroxide → HCID 22225582, compound

HRID 2288229Notes

Reaction equation

HRID 2288229 reaction equation
[C:1]1([C:7](=[CH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:18].[Na+].OO.[Cl-].[Na+]>CO>[C:1]1([C:7]2([O:18][CH:11]2[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:8](=[O:10])[CH3:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 53943003HCID 53943003, compound

Product 1

HCID 22225582HCID 22225582, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-phenyl-4-(4-pyridyl)-3-butene-2-one (step 1) (500 mg, 2.24 mmol) in methanol (10 ml) at room temperature was added an aqueous solution (9 ml) of sodium hydroxide (100 mg, 2.24 mmol) and hydrogen peroxide (0.5 ml of 30% aqueous solution, 4.4 mmol). After stirring for 2 hours, sodium chloride was added and the reaction was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to provide the crude 3-phenyl-4-(4-pyridyl)-3,4-epoxy-2-butanone (385 mg, 65%) as an oil. This was used in the next step without further purification.

Workup

  1. extractionthe reaction was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7e9e6fc645d4b669d0e05458f034dc8
Source dataset
uspto-grants-2000_07
Patent number
US06087496

Reaction notes

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