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

HRID 1382803

반응식

HRID 1382803 반응식
[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

참가 물질

5

반응물 3

HCID 69201Ethyl 3-furoateHCID 321710OxindoleHCID 5360545Sodium

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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, m.p. 185°-186° C.

후처리

  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

출처 및 근거

ORD 기록
ord-15e3fe518ec042c3b9bae9199f172d68
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04808601

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