Chloride → HCID 54090937, Verbindung

HRID 478153

Reaktionsgleichung

Reaktionsgleichung von HRID 478153
[Cl-].C([Li])CCC.[CH2:7]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10].[Cl-].[Na+].[CH2:21]([O:23][CH2:24]C)C>>[CH2:7]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[CH:21][O:23][CH3:24])=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10]

Komponenten

6

Edukt 5

HCID 312ChlorideHCID 3283Diethyl Ether2×HCID 5234Sodium ChlorideHCID 709884-ButylbenzaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 54090937HCID 54090937, Verbindung

Versuchsvorschrift

21.1 g of methoxymethyltriphnylphosphonium chloride is introduced into 280 ml of diethyl ether under nitrogen. At 0° C., 29.6 ml of n-butyllithium solution (1.6 M in hexane) is added in drops, and it is stirred for one hour at room temperature. 10 g of 4-butylbenzaldehyde in 40 ml of diethyl ether is now added, and it is stirred for one more hour. Sodium chloride solution is added to the reaction mixture, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. After chromatography on silica gel with ethyl acetate, 6.7 g of 2-(4-butylphenyl)-1-methoxyethene 48 (E,Z-mixture) is obtained as a colorless oil, which is dissolved in 200 ml of acetone and is stirred under nitrogen with 10 ml of 2N hydrochloric acid overnight. Sodium chloride solution is added, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. Chromatographic purification on silica gel with ethyl acetate/hexane yields 3.9 g of title compound 49 as a colorless oil.

Aufarbeitung

  1. stirringit is stirred for one more hour
  2. extractionextracted with ethyl acetate
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0e01be7156c34bd5a535ddd6a87dc8c5
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642218B2

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