Ethyl Acetate → 3-Isopropyl-5-(4-nitro-2,6-dimethyl-phenoxy)-1H-indole

HRID 1007484

Reaktionsgleichung

Reaktionsgleichung von HRID 1007484
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[CH:22]=[C:23]([N+:29]([O-:31])=[O:30])[CH:24]=[C:25]([CH3:28])[C:26]=1F.C(OCC)(=O)C>CS(C)=O.O>[CH:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][C:26]3[C:21]([CH3:20])=[CH:22][C:23]([N+:29]([O-:31])=[O:30])=[CH:24][C:25]=3[CH3:28])[CH:3]=2)[NH:7][CH:6]=1)([CH3:13])[CH3:12]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 113672322-Fluoro-1,3-dimethyl-5-nitrobenzeneHCID 226694913-isopropyl-1H-indol-5-ol

Produkt 1

HCID 226695113-Isopropyl-5-(4-nitro-2,6-dimethyl-phenoxy)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

11.44 g (58.76 mmol) of 5-hydroxy-3-isopropyl-indole are dissolved in 350 ml of DMSO, 8.93 g (64.63 mmol) of potassium carbonate in solid form are introduced and subsequently 9.94 g (58.76 mmol) of 3,5-dimethyl-4-fluoronitrobenzene are added. The reaction solution is stirred for 2 hours at 100° C. under argon. Afterwards it is cooled to room temperature, 100 ml of ethyl acetate and 600 ml of H2O are added; ethyl acetate is separated off after phase separation and the aqueous phase is reextracted twice with ethyl acetate. The combined organic phases are washed twice with sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness. The residue is purified by chromatography on silica gel by means of cyclohexane/ethyl acetate (10:1).

Aufarbeitung

  1. temperatureAfterwards it is cooled to room temperature
  2. customethyl acetate is separated off
  3. customafter phase separation
  4. washThe combined organic phases are washed twice with sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue is purified by chromatography on silica gel by means of cyclohexane/ethyl acetate (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-c65647b50728423e988ab1d275144b03
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794406B2

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