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

HRID 1440337Notes

Reaction equation

HRID 1440337 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]=[O:13])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].Br[C:16](=[CH:18][CH3:19])[CH3:17].[Cl-].[NH4+]>O1CCCC1.O>[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]([OH:13])[C:16]([CH3:17])=[CH:18][CH3:19])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 209102-Bromobut-2-eneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 113672673-Phenyl-1,2-oxazole-5-carbaldehyde

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.0 g (28.9 mmol) of 3-phenyl-isoxazole-5-aldehyde in 40 ml of tetrahydrofuran, was added dropwise at -30° C. a solution of 1.5 g of metallic magnesium and 10.1 g (74.8 mmol) of 2-bromo-2-butene in 80 ml of tetrahydrofuran. After they were reacted at the same temperature for 30 minutes, the temperature of the reaction mixture was allowed to rise to room temperature and a saturated aqueous solution of ammonium chloride was added to terminate the reaction. Water was added, followed by extraction with ethyl ether. The organic layer was successively washed with water and saturated saline and then dried over anhydrous sodium sulfate. After ethyl ether was distilled off, the residue was purified by chromatography on a silica gel column (eluent: 9:1 hexane/ethyl acetate) so that 3-phenyl-5-(1-hydroxy-2-methyl-2-butenyl)isoxazole was obtained as oil.

Workup

  1. customAfter they were reacted at the same temperature for 30 minutes
  2. customto rise to room temperature
  3. customto terminate
  4. customthe reaction
  5. extractionfollowed by extraction with ethyl ether
  6. washThe organic layer was successively washed with water and saturated saline
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter ethyl ether was distilled off
  9. customthe residue was purified by chromatography on a silica gel column (eluent: 9:1 hexane/ethyl acetate) so that 3-phenyl-5-(1-hydroxy-2-methyl-2-butenyl)isoxazole
  10. customwas obtained as oil

Sources & evidence

ORD record
ord-bdf087cc2f9a4c1682eec862b99bdf8c
Source dataset
uspto-grants-1996_03
Patent number
US05498619

Reaction notes

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