Methyl iodide → 1-(1-Methyl-1H-indol-3-yl)ethanone

HRID 362791

Reaktionsgleichung

Reaktionsgleichung von HRID 362791
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:15]I>C1COCC1>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:15])[CH:5]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 128023-AcetylindoleHCID 24758Sodium hydride

Produkt 1

HCID 5941561-(1-Methyl-1H-indol-3-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Acetyl-1H-indole (4.00 g, 0.025 mol) was dissolved in dry THF (100 ml), and treated with 80% sodium hydride (0.794 g, 0.0263 mol) with stirring under Ar. After 0.5 h, methyl iodide (2.36 ml, 0.038 mol) was added. After 20 h, the reaction mixture was evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was then dried (Na2SO4), and evaporated under reduced pressure to give the title compound as a pale brown oil which crystallised on standing (4.20 g, 97%).

Aufarbeitung

  1. waitAfter 20 h
  2. customthe reaction mixture was evaporated under reduced pressure
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was then dried (Na2SO4)
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-91a523413b884541b67862091b944cc1
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872134

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