1-(Triphenylphosphoranylidene)acetone → Methyl 3-(3-oxo-1-butenyl)indole-6-carboxylate

HRID 278098

Reaktionsgleichung

Reaktionsgleichung von HRID 278098
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=O.[C:16]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:18])[CH3:17]>O1CCOCC1>[O:18]=[C:16]([CH3:19])[CH:17]=[CH:1][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 735867methyl 3-formyl-1H-indole-6-carboxylate

Produkt 1

HCID 53858282Methyl 3-(3-oxo-1-butenyl)indole-6-carboxylateAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 3-formylindole-6-carboxylate (368 mg) in 1,4-dioxane (10 ml) was added acetylmethylene triphenylphosphorane (1.15 g), and the mixture was stirred under reflux for 12 hours. The resulting mixture was evaporated in vacuo, redissolved with ethyl acetate and washed with 1N hydrochloric acid and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of chloroform and ethyl acetate (1:2) to give methyl 3-(3-oxo-1-butenyl)indole-6-carboxylate (75 mg) as a solid.

Aufarbeitung

  1. temperatureunder reflux for 12 hours
  2. customThe resulting mixture was evaporated in vacuo
  3. dissolutionredissolved with ethyl acetate
  4. washwashed with 1N hydrochloric acid and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with a mixture of chloroform and ethyl acetate (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-e5b7b3b9a0b94d1a9039241ad2e1a667
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358992B1

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