Pentyltriphenylphosphonium bromide → 1-(4-Nonylphenyl)-hex-1-ene

HRID 1382699

Reaktionsgleichung

Reaktionsgleichung von HRID 1382699
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH3:6].C([Li])CCC.[CH2:31]([C:40]1[CH:47]=[CH:46][C:43]([CH:44]=O)=[CH:42][CH:41]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>O1CCCC1.CCCCCC>[CH2:31]([C:40]1[CH:47]=[CH:46][C:43]([CH:44]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:42][CH:41]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Komponenten

6

Edukt 3

HCID 2724565Pentyltriphenylphosphonium bromideHCID 109333644-NonylbenzaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 536769591-(4-Nonylphenyl)-hex-1-ene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A suspension of 13.9 g of pentyltriphenylphosphonium bromide in 150 ml of tetrahydrofuran is cooled to -20° under argon, 21.2 ml of 1.6M butyllithium solution in hexane are added within a period of 5 minutes and the whole is stirred for a further 30 minutes at 0°-10°. 6 g of 4-nonylbenzaldehyde in 40 ml of tetrahydrofuran are added dropwise over a period of 30 minutes to the mixture, which has been cooled to from -60° to -70°. The reaction mixture is allowed to warm spontaneously to 0°-10°, stirred at this temperature for a further 45 minutes and concentrated by evaporation. The residue is taken up in hexane/ethyl acetate (1:) and filtered over silica gel. The filtrate is concentrated by evaporation and chromatographed on silica gel with hexane. The title compound (mixture of cis- and trans-isomers) is obtained in the form of a colourless oil, which is used directly in the next stage.

Aufarbeitung

  1. temperatureis cooled to -20° under argon
  2. temperaturehas been cooled to from -60° to -70°
  3. temperatureto warm spontaneously to 0°-10°
  4. stirringstirred at this temperature for a further 45 minutes
  5. concentrationconcentrated by evaporation
  6. filtrationfiltered over silica gel
  7. concentrationThe filtrate is concentrated by evaporation
  8. customchromatographed on silica gel with hexane

Quellen und Nachweise

ORD-Eintrag
ord-1684badff4fe41d6879673bc35815f6b
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808572

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