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

HRID 1440338Notes

Reaction equation

HRID 1440338 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 ml 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-2butenoyl)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-35fdcf50b1d54ae2aa2961d3d091ecc9
Source dataset
uspto-grants-1996_03
Patent number
US05498619

Reaction notes

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