Sodium hydride → HCID 86612915, Verbindung

HRID 1445888

Reaktionsgleichung

Reaktionsgleichung von HRID 1445888
[H-].[Na+].[CH2:3]([O:10][C:11](=[O:24])[CH2:12][O:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]([CH3:23])[NH:18]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:25][CH:26](Br)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([O:10][C:11](=[O:24])[CH2:12][O:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]([CH3:23])[N:18]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][Br:25])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 113249061,1-DibromododecaneHCID 58765424HCID 58765424, Verbindung

Produkt 1

HCID 86612915HCID 86612915, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (60% in mineral oil, 0.093 g, 6.45 mmole) in DMF (10 mL), (2-methyl-1H-indol-4-yloxy)-acetic acid benzyl ester (2) (0.845 g, 2.3 mmole) was added. The mixture was stirred at room temperature for 1 h. To the mixture, dibromododecane (0.765 g, 2.3 mmole) was added and the reaction mixture was stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate and washed with water. The organic layer was separated, dried with sodium sulphate and concentrated. The residue was purified by column chromatography (10:1, hexane: EtOAc) to afford intermediate 3. Yield: 0.708 g, 45%.

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for 18 h
  3. washwashed with water
  4. customThe organic layer was separated
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (10:1, hexane: EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e4ca5912b9f34cb28c09fa906118453e
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666898B2

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