1-Bromo-2-methylpropane → 3-Phenyl-5-(3-methylbutyryl)isoxazole

HRID 1450654Notes

Reaction equation

HRID 1450654 reaction equation
[CH2:1]([Mg]Br)[CH:2]([CH3:4])[CH3:3].[Mg].[CH2:8](Br)[CH:9]([CH3:11])[CH3:10].[Cl-].[NH4+:14].[CH3:15][C:16]([CH3:18])=[O:17].OS(O)(=O)=O.[O:24]=[Cr](=O)=O.O1C[CH2:31][CH2:30][CH2:29]1>CC(C)=O.C(O)(C)C.O>[C:2]1([C:4]2[CH:15]=[C:16]([C:18](=[O:24])[CH2:8][CH:9]([CH3:11])[CH3:10])[O:17][N:14]=2)[CH:3]=[CH:31][CH:30]=[CH:29][CH:1]=1

Participants

10

Reactant 6

HCID 65551-Bromo-2-methylpropaneHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 131709961Jones' reagent2×HCID 178418816HCID 178418816, compound

Product 1

HCID 151807673-Phenyl-5-(3-methylbutyryl)isoxazole

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 5.0 g (28.9 mmol) of the aldehyde derivative (3-phenylisoxazole-5-aldehyde), which had been prepared above in the procedure (1), in 40 ml of tetrahydrofuran, was added dropwise at -50° C. to -30° C. a solution of isobutylmagnesium bromide, which had been prepared from 1.4 g of metallic magnesium and 7.9 g (57.7 mmol) of isobutyl bromide, in 80 ml of tetrahydrofuran. After completion of the dropwise addition, they were reacted for 1 hour at the same temperature. Thereafter, a saturated aqueous solution of ammonium chloride was added. The reaction mixture was added into water and then extracted with diethyl ether. The solvent was distilled off. An oily residue thus obtained was dissolved in 50 ml of acetone, followed by the oxidation with the Jones' reagent under ice cooling. Isopropyl alcohol was added to react the same with the Jones' reagent, and an insoluble material was then filtered off. After substantial removal of acetone by distillation, the residue was added into water and then extracted with ethyl acetate. Subsequent removal of the solvent by distillation, the residue was purified by silica gel chromatography (eluent: chloroform) so that 3-phenyl-5-(3-methylbutyryl)isoxazole was obtained as crystals.

Workup

  1. additionAfter completion of the dropwise addition, they
  2. customwere reacted for 1 hour at the same temperature
  3. extractionextracted with diethyl ether
  4. distillationThe solvent was distilled off
  5. customAn oily residue thus obtained
  6. filtrationan insoluble material was then filtered off
  7. customAfter substantial removal of acetone
  8. distillationby distillation
  9. additionthe residue was added into water
  10. extractionextracted with ethyl acetate
  11. customSubsequent removal of the solvent
  12. distillationby distillation
  13. customthe residue was purified by silica gel chromatography (eluent: chloroform) so that 3-phenyl-5-(3-methylbutyryl)isoxazole
  14. customwas obtained as crystals

Sources & evidence

ORD record
ord-757a8e9f63044fdcbab3535be579d12b
Source dataset
uspto-grants-1997_02
Patent number
US05602160

Reaction notes

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