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 522478Notes

Reaction equation

HRID 522478 reaction equation
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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-be4e3687e7344c829c29309dac98d638
Source dataset
uspto-grants-2016_05
Patent number
US09333205B2

Reaction notes

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