Hydroxylamine monohydrate → Ethyl 7-ethoxy-7a-hydroxy-3a,4,5,7a-tetrahydro-1,2-benzisoxazole-3-carboxylate

HRID 522477Notes

Reaction equation

HRID 522477 reaction equation
[CH2:1]([O:3][C:4]1[C:5](=[O:17])[CH:6]([C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8][CH:9]=1)[CH3:2].[OH:18][NH2:19].O>CCO.CC(O)=O>[CH2:1]([O:3][C:4]1[C:5]2([OH:17])[CH:6]([C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:19][O:18]2)[CH2:7][CH2:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 2

HCID 22235265Hydroxylamine monohydrateHCID 44235432Ethyl (3-ethoxy-2-oxocyclohex-3-en-1-yl)(oxo)acetate

Product 1

HCID 66714068Ethyl 7-ethoxy-7a-hydroxy-3a,4,5,7a-tetrahydro-1,2-benzisoxazole-3-carboxylateYield 25%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of ethyl (3-ethoxy-2-oxocyclohex-3-en-1-yl)(oxo)acetate 5.0 g (20.73 mmol) in 20 mL of EtOH and 5 mL of AcOH, 1.3 mL (20.78 mmol) of HONH2.H2O (50% wt/wt) was added. The mixture was stirred at room temperature for 4 hours. 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 1.35 g (25% yield) as a white solid of ethyl 7-ethoxy-7a-hydroxy-3a,4,5,7a-tetrahydro-1,2-benzisoxazole-3-carboxylate

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude solid was purified by flash chromatography on silica gel (eluant: AcOEt/Hexane:3/7)

Sources & evidence

ORD record
ord-f1d900db82814b068393d1fa7a53d4bc
Source dataset
uspto-grants-2016_05
Patent number
US09333205B2

Reaction notes

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