Ethyl Acetate → N-(2,5-Dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide

HRID 413349Notes

Reaction equation

HRID 413349 reaction equation
[O:1]1[CH:7]2[CH:2]1[C:3](OC)([O:19]C)[C:4]([NH:9][C:10](=[O:18])[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13])=[CH:5][C:6]2=[O:8].C(OCC)(=O)C>C(Cl)Cl>[O:1]1[CH:2]2[CH:7]1[C:6](=[O:8])[CH:5]=[C:4]([NH:9][C:10](=[O:18])[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13])[C:3]2=[O:19]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 12043282N-(2,2-dimethoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide

Product 1

HCID 9859948N-(2,5-Dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamideYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,6-Epoxy-4,4-dimethoxy-3-salicyloylamino-2-cyclohexenone (1.0 g, 3.27 mmol) was dissolved in methylene chloride (25 ml), trifluoroboron diethyl ether complex (1 ml) was added thereto under ice cooling, and the mixture was stirred at the same temperature as described above for 30 minutes. Ethyl acetate (300 ml) was added to the reaction mixture and the reaction mixture was washed with water (200 ml). After drying it over Glauber's salt, the ethyl acetate layer was dried under vacuum to obtain brown solids, which were washed with methanol (5 ml) to obtain the titled compound (399 mg) as pale brown solids (yield: 47%).

Workup

  1. additiontrifluoroboron diethyl ether complex (1 ml) was added
  2. customas described above for 30 minutes
  3. washthe reaction mixture was washed with water (200 ml)
  4. dry with materialAfter drying it over Glauber's salt
  5. dry with materialthe ethyl acetate layer was dried under vacuum
  6. customto obtain brown solids, which
  7. washwere washed with methanol (5 ml)

Sources & evidence

ORD record
ord-7634c35f59cc4cb6a1e8c2bb92872330
Source dataset
uspto-grants-2003_05
Patent number
US06566394B1

Reaction notes

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