Ethyl 3-furoate → 3-(3-Furoyl)-2-oxindole

HRID 978702

Reaction equation

HRID 978702 reaction equation
[Na].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:11].[O:12]1[CH:16]=[CH:15][C:14]([C:17](OCC)=[O:18])=[CH:13]1>C(O)C>[O:12]1[CH:16]=[CH:15][C:14]([C:17]([CH:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:2][C:3]2=[O:11])=[O:18])=[CH:13]1

Participants

5

Reactant 3

HCID 69201Ethyl 3-furoateHCID 321710OxindoleHCID 5360545Sodium

Product 1

HCID 135656573-(3-Furoyl)-2-oxindoleYield 3.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2.8 g (0.12 mole) of sodium in 200 ml of ethanol was added 13.3 g (0.10 mole) of 2-oxindole, followed by 16.8 g of ethyl 3-furoate. The mixture was heated under reflux for 47 hours, cooled and then the solvent was removed by evaporation in vacuo. The residue was triturated under 200 ml of ether, and the solid was collected by filtration and discarded. The filtrate was evaporated in vacuo, and the residue triturated under isopropyl alcohol and recovered by filtration. The solid was suspended in 250 ml of water, which was then acidified with concentrated hydrochloric acid. This mixture was stirred to give a solid, which was recovered by filtration. This latter solid was recrystallized from acetic acid followed by acetonitrile to give 705 mg of the title compound, mp 185°-186° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 47 hours
  3. temperaturecooled
  4. customthe solvent was removed by evaporation in vacuo
  5. customThe residue was triturated under 200 ml of ether
  6. filtrationthe solid was collected by filtration
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue triturated under isopropyl alcohol
  9. filtrationrecovered by filtration
  10. customto give a solid, which
  11. filtrationwas recovered by filtration
  12. customThis latter solid was recrystallized from acetic acid

Sources & evidence

ORD record
ord-6f5a5d4337314a3fad5c2a1e3d7adbf0
Source dataset
uspto-grants-1987_05
Patent number
US04665194

Linked notes

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