Hydrogen Peroxide → 4-Phenyl-3-(4-pyridyl)-3,4-epoxy-2-butanone

HRID 1167509Notes

Reaction equation

HRID 1167509 reaction equation
[C:1]1([CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:9](=[O:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:18]O.[OH-].[Na+]>CO>[C:1]1([CH:7]2[O:18][C:8]2([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:9](=[O:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 538852224-Phenyl-3-(4-pyridyl)-3-butene-2-one

Product 1

HCID 220376354-Phenyl-3-(4-pyridyl)-3,4-epoxy-2-butanoneYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the procedure of Example A-1, step 2, a solution of 4-phenyl-3-(4-pyridyl)-3-butene-2-one (step 2) (1.25 g, 5.6 mmol) in methanol (20 ml) was treated with 30% aqueous hydrogen peroxide (1 ml) in the presence of sodium hydroxide (230 mg, 5.7 mmol). The crude product was purified by chromatography (silica gel, 1:1 ethyl acetate/hexane) to give 4-phenyl-3-(4-pyridyl)-3,4-epoxy-2-butanone (270 mg, 20%).

Workup

  1. customThe crude product was purified by chromatography (silica gel, 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3c9044fe8e054670a979ce73f9a733e3
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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