Ethanol → HCID 20338041, compound

HRID 1395751Notes

Reaction equation

HRID 1395751 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C:4]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18](N)=[O:19])=[CH:16][C:3]1=2.[CH2:22]([OH:24])[CH3:23]>S(=O)(=O)(O)O>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C:4]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18]([O:24][CH2:22][CH3:23])=[O:19])=[CH:16][C:3]1=2

Participants

4

Reactant 2

HCID 702EthanolHCID 20338062HCID 20338062, compound

Product 1

HCID 20338041HCID 20338041, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To 62 mg of 2-(10,11-dihydro-11-oxo dibenzo[b,f]oxepin-2-yl)-propionamide in 2 ml of ethanol were added three drops of conc. sulfuric acid and the mixture was reluxed with stirring for 4 hours. After the completion of the reaction, the solvent was distilled off to obtain the residue, to which was added ice and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogencarbonate solution, then saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain brown oil, which was chromatographed over silica gel, eluted with chloroform and there was obtained 58 mg of ethyl 2-(10,11-dihydro-11-oxo dibenzo[b,f]oxepin-2-yl)-propionate as pale yellow oil.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe solvent was distilled off
  3. customto obtain the residue
  4. additionto which was added ice
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated sodium hydrogencarbonate solution
  7. dry with materialsaturated sodium chloride solution and dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customto obtain brown oil, which
  10. customwas chromatographed over silica gel
  11. washeluted with chloroform

Sources & evidence

ORD record
ord-c991e67261974a1cb65eea52b545a812
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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