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

HRID 1440337

Reaktionsgleichung

Reaktionsgleichung von HRID 1440337
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bdf087cc2f9a4c1682eec862b99bdf8c
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05498619

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