1-Butanaminium, N,N,N-tributyl-, azide → HCID 86641873, Verbindung

HRID 561014

Reaktionsgleichung

Reaktionsgleichung von HRID 561014
CCCC[N+](CCCC)(CCCC)CCCC.[N-:18]=[N+:19]=[N-:20].[F:21][C:22]1[N:27]=[CH:26][C:25]([CH:28](O)[CH3:29])=[C:24]([I:31])[CH:23]=1>ClCCl>[N:18]([CH:28]([C:25]1[C:24]([I:31])=[CH:23][C:22]([F:21])=[N:27][CH:26]=1)[CH3:29])=[N+:19]=[N-:20]

Komponenten

4

Edukt 2

HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 66738096HCID 66738096, Verbindung

Produkt 1

HCID 86641873HCID 86641873, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add tetra-N-butylammonium azide to a solution of triphenylphine (11 g, 42 mmol) and 1,4-cyclohexadiene-2,2-dicarbonitrile,4,5-dichloro-3,6-dioxo-(9 g, 40 mmol) in dichloromethane (150 mL) under ice-bath cooling. Then add 1-(6-fluoro-4-iodo-pyridin-3-yl)-ethanol (6.7 g, 25.1 mmol) to the above solution. Stir the mixture at room temperature for 1 hour. Concentrate the mixture in vacuo to about 50 mL. Purify the residue by flash column chromatography (hexane to 20% ethyl acetate in hexane as gradient) to give target product as colorless oil (5.7 g, 78%). MS (ES) m/z 293 [M+1]+.

Aufarbeitung

  1. temperaturecooling
  2. concentrationConcentrate the mixture in vacuo to about 50 mL
  3. customPurify the residue by flash column chromatography (hexane to 20% ethyl acetate in hexane as gradient)

Quellen und Nachweise

ORD-Eintrag
ord-ca10d2d06b1b47eca7dfca38dbf2c0ce
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063212B2

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