Water → HCID 19390157, Verbindung

HRID 1757273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1757273
[Br-].[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].[H-].[Na+].[S:29]1[CH:33]=[CH:32][C:31]([C:34]2[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=2)[CH:37]=O)=[CH:30]1.O>CN(C)C=O.C(O)(=O)C>[C:2]([CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:37]/[C:36]1[CH:35]=[C:34]([C:31]2[CH:32]=[CH:33][S:29][CH:30]=2)[CH:41]=[CH:40][CH:39]=1)#[N:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 45475263-(Thiophen-3-yl)benzaldehydeHCID 11418829(4-Cyanobutyl)(triphenyl)phosphanium bromide

Produkt 1

HCID 19390157HCID 19390157, VerbindungAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

44.6 g of 4-cyanobutyl(triphenyl)phosphonium bromide is suspended in 250 ml of dimethylformamide, 4.2 g of 60% oily sodium hydride is added under ice cooling and stirring, the mixture is stirred at that temperature for 30 minutes, 18 g of 3-(3-thienyl)benzaldehyde is added, and the mixture is stirred at room temperature for 20 hours. Water and acetic acid are added to the reaction solution for neutralization, the solvent is distilled off under reduced pressure, and the residue is post-treated in a conventional manner and purified by silica gel column chromatography [Wako gel C-100, 500 g; hexane/ethyl acetate=5/1] to obtain 23.2 g of (E)-3-[3-(5-cyano-1-pentenyl)phenyl]thiophene as colorless oil.

Aufarbeitung

  1. stirringthe mixture is stirred at that temperature for 30 minutes
  2. stirringthe mixture is stirred at room temperature for 20 hours
  3. distillationthe solvent is distilled off under reduced pressure
  4. additionthe residue is post-treated in a conventional manner
  5. custompurified by silica gel column chromatography [Wako gel C-100, 500 g; hexane/ethyl acetate=5/1]

Quellen und Nachweise

ORD-Eintrag
ord-957ecab288764102a76686b5d4bdb67c
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05444084

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