Ethanol → HCID 20337909, compound

HRID 1395687Notes

Reaction equation

HRID 1395687 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][CH:17]([C:19]([OH:21])=[O:20])[CH2:16][C:15]=3[CH:22]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH2:23](O)[CH3:24]>S(=O)(=O)(O)O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][CH:17]([C:19]([O:21][CH2:23][CH3:24])=[O:20])[CH2:16][C:15]=3[CH:22]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 20337914HCID 20337914, compound

Product 1

HCID 20337909HCID 20337909, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

5 drops of concentrated sulfuric acid was added to a mixture of 3.2 g of 7C and 150 ml of ethanol. The mixture was heated under reflux, using a Soxhlet extractor filled with molecular sieve (3A). After 4 hours, the solvent was evaporated under reduced pressure, and the residue was dissolved in chloroform. The solution was washed with saturated sodium bicarbonate solution, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was dry column chromatographed over silica gel, using chloroform as eluent. The product was extracted with tetrahydrofuran and the solvent was evaporated under reduced pressure. The residue was stirred in ether. The solid was collected and refluxed in ether. The solid was collected and dried under reduced pressure to give ethyl 5-(4-(acetylamino)phenyl)-2,3-dihydro-2-benzofurancarboxylate (7D), mp: 164°-166° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform
  5. washThe solution was washed with saturated sodium bicarbonate solution
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was dry column
  9. customchromatographed over silica gel
  10. extractionThe product was extracted with tetrahydrofuran
  11. customthe solvent was evaporated under reduced pressure
  12. customThe solid was collected
  13. temperaturerefluxed in ether
  14. customThe solid was collected
  15. customdried under reduced pressure

Sources & evidence

ORD record
ord-b51a717c43a7480ab60d1bc18f6b48a1
Source dataset
uspto-grants-1980_05
Patent number
US04205080

Reaction notes

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