Ethyl 7-ethoxy-7a-hydroxy-3a,4,5,7a-tetrahydro-1,2-benzisoxazole-3-carboxylate → Ethyl 7-oxo-4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxylate

HRID 522478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522478
C([O:3][C:4]1[C:12]2(O)[CH:8]([C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:10][O:11]2)[CH2:7][CH2:6][CH:5]=1)C>CCO.Cl>[O:3]=[C:4]1[C:12]2[O:11][N:10]=[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]=2[CH2:7][CH2:6][CH2:5]1

Komponenten

4

Edukt 1

HCID 66714068Ethyl 7-ethoxy-7a-hydroxy-3a,4,5,7a-tetrahydro-1,2-benzisoxazole-3-carboxylate

Produkt 1

HCID 66713797Ethyl 7-oxo-4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxylateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 7-ethoxy-7a-hydroxy-3a,4,5,7a-tetrahydro-1,2-benzisoxazole-3-carboxylate 3.18 g (12.48 mmol) in 30 mL of EtOH, 3 mL of HCl 36% was added. The mixture was stirred at reflux for 48 hours. After cooling the solvent was removed under reduced pressure and the crude solid was purified by flash chromatography on silica gel (eluant: AcOEt/Hexane 3/7) to afford 1.3 g (50% yield) of the title compound as a white solid.

Aufarbeitung

  1. temperatureat reflux for 48 hours
  2. temperatureAfter cooling the solvent
  3. customwas removed under reduced pressure
  4. customthe crude solid was purified by flash chromatography on silica gel (eluant: AcOEt/Hexane 3/7)

Quellen und Nachweise

ORD-Eintrag
ord-be4e3687e7344c829c29309dac98d638
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09333205B2

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