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

HRID 1742541Notes

Reaction equation

HRID 1742541 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. Analytical results of the crystals obtained: Yield: 3.6 g (67%).

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-ee1018622db04ba3bc27d027400064c5
Source dataset
uspto-grants-1994_08
Patent number
US05338857

Reaction notes

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