Pentyltriphenylphosphonium bromide → 5-Chloro-2-hex-1-enyl-1H-indole

HRID 2406662

Reaktionsgleichung

Reaktionsgleichung von HRID 2406662
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH3:6].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41]([CH:46]=O)=[CH:40]2>C1COCC1>[Cl:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41]([CH:46]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:40]2

Komponenten

5

Edukt 3

HCID 2724565Pentyltriphenylphosphonium bromideHCID 2733832Lithium HexamethyldisilazideHCID 122033185-Chloro-1H-indole-2-carbaldehyde

Produkt 1

HCID 687508525-Chloro-2-hex-1-enyl-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To the cold suspension of pentyl triphenyl-phosphonium bromide in THF was added LiHMDS in THF and the mixture was stirred for 30 minutes and then the solution of 5-chloro-1H-indole-2-carbaldehyde was added to the reaction mixture and stirred for 3 hours. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The product, 5-chloro-2-hex-1-enyl-1H-indole was purified by column chromatography.

Aufarbeitung

  1. stirringstirred for 3 hours
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. customThe product, 5-chloro-2-hex-1-enyl-1H-indole was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a4fadc70ddac419fb5aff51eaf4d3d05
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809382B2

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