Potassium Carbonate → Ethyl 4-[3-[8-(4-isobutylphenyl)undecanoyl]1-indolyl]butyrate

HRID 260840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 260840
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:29][CH2:30][CH3:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:19])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].Br[CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH2:29][CH2:30][CH3:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:21]=2)=[O:19])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 22400457HCID 22400457, Verbindung

Produkt 1

HCID 22400460Ethyl 4-[3-[8-(4-isobutylphenyl)undecanoyl]1-indolyl]butyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-[8-(4-isobutylphenyl)undecanoyl]indole obtained in Pre. Ex. 8 (62 mg), ethyl 4-bromobutyrate (58 mg) and potassium carbonate (62 mg) in N,N-dimethylformamide (2 ml) was stirred at room temperature for 16 hours. After filtration, the solution was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on a silica gel column (hexane-ethyl acetate, 4: 1) to give ethyl 4-[3-[8-(4-isobutylphenyl)-undecanoyl]-1-indolyl]butyrate as an oil. (48 mg)

Aufarbeitung

  1. customobtained in Pre
  2. filtrationAfter filtration
  3. additionthe solution was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column (hexane-ethyl acetate, 4: 1)

Quellen und Nachweise

ORD-Eintrag
ord-bf73e613be28460fb1f50d29b4957514
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530019

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