Hydrochloric Acid → Ethyl 1,2,3,4-tetrahydro-5-oxo-benz[b]oxepine-4-carboxylate

HRID 840965Notes

Reaction equation

HRID 840965 reaction equation
C(O[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:5])C.[H-].[Na+].C(O)C.Cl>C1(C)C=CC=CC=1>[O:5]=[C:4]1[CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][O:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 24758Sodium hydrideHCID 15486834HCID 15486834, compound

Product 1

HCID 15486835Ethyl 1,2,3,4-tetrahydro-5-oxo-benz[b]oxepine-4-carboxylateYield 83.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
82.5 °C

Procedure

A mixture of ethyl 4-(2-ethoxycarbonylphenyloxy)-butyrate (13.0 g, 46.4 mmol), 60% sodium hydride (5.56 g, 139 mmol), ethanol (2.5 ml) and toluene (250 ml) was stirred at 80-85° C. for 2 hours. The reaction mixture was poured into cold 1N hydrochloric acid and extracted twice with ethyl acetate, and the extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; ethyl acetate:n-hexane=3:97) to obtain 9.05 g of ethyl 1,2,3,4-tetrahydro-5-oxo-benz[b]oxepine-4-carboxylate.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washthe extract solution was washed with a 5% aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent; ethyl acetate:n-hexane=3:97)

Sources & evidence

ORD record
ord-7489b2e3395446a59c8f89f525cdea19
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

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