3-Phenyl-5-(1-hydroxy-2-methyl-2-butenyl)isoxazole → 3-Phenyl-5-(2-methyl-2-butenoyl)isoxazole

HRID 1450659Notes

Reaction equation

HRID 1450659 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]([OH:17])[C:13]([CH3:16])=[CH:14][CH3:15])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[C:1]1([C:7]2[CH:11]=[C:10]([C:12](=[O:17])[C:13]([CH3:16])=[CH:14][CH3:15])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 536910293-Phenyl-5-(1-hydroxy-2-methyl-2-butenyl)isoxazole

Product 1

HCID 539504603-Phenyl-5-(2-methyl-2-butenoyl)isoxazole

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

Dissolved in 100 m of benzene were 5.4 g (23.6 mmol) of 3 -phenyl-5-(1-hydroxy-2 -methyl-2 -butenyl)isoxazole, followed by the addition of 21.0 g (0.24 mol) of manganese dioxide. The mixture was stirred at room temperature for 24 hours. An insoluble material was filtered off and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: 30:1 n-hexane/ethyl acetate), whereby 3-phenyl-5-(2-methyl-2-butenoyl)isoxazole was obtained as colorless oil.

Workup

  1. filtrationAn insoluble material was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel chromatography (eluent: 30:1 n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8fadf0e05ca34cef9cbee07dd3d072ca
Source dataset
uspto-grants-1997_02
Patent number
US05602160

Reaction notes

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