(E)-N-[2-(6-methoxyindan-1-ylidene)ethyl]acetamide → N-[2-(5-Methoxy-1H-inden-3-yl)ethyl]acetamide

HRID 582210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582210
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8]/[C:9]/2=[CH:12]\[CH2:13][NH:14][C:15](=[O:17])[CH3:16])=[CH:5][CH:4]=1>FC(F)(F)C(O)=O.O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6](=[CH:5][CH:4]=1)[CH2:7][CH:8]=[C:9]2[CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16]

Komponenten

5

Edukt 1

HCID 59957023(E)-N-[2-(6-methoxyindan-1-ylidene)ethyl]acetamide

Produkt 1

HCID 54016815N-[2-(5-Methoxy-1H-inden-3-yl)ethyl]acetamideAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The (E)-N-[2-(6-methoxyindan-1-ylidene)ethyl]-acetamide (1.0 g, 4.32 mmol) thus obtained was dissolved in trifluoroacetic acid(6 ml)-tetrahydrofuran(6 ml) and the solution was refluxed for 1.5 hours. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed serially with saturated saline and water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-methanol=96:4) to provide the title compound (yield 0.9 g, 90%).

Aufarbeitung

  1. temperaturethe solution was refluxed for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed serially with saturated saline and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-methanol=96:4)

Quellen und Nachweise

ORD-Eintrag
ord-4565cd77d32543e7903de635a35c357a
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922771

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