Hexane → 5-Phenylpent-4-enyl-1-ol

HRID 477010

Reaktionsgleichung

Reaktionsgleichung von HRID 477010
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[OH:12][CH:13]1CCCO1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:3]1(/[CH:10]=[CH:9]/[CH2:8][CH2:7][CH2:13][OH:12])[CH:2]=[CH:1][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 8058HexaneHCID 93002Tetrahydro-2-hydroxyfuranHCID 178418339Butyllithium

Produkt 1

HCID 53716955-Phenylpent-4-enyl-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 70671Benzyltriphenylphosphonium chlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 4 g of benzyltriphenylphosphonium chloride in 20 ml of tetrahydrofuran was added 7.07 ml of 1.6M hexane solution of n-butyl lithium under cooling at 0° C. After stirring at room temperature for 30 minutes, 1 g of 2-hydroxytetrahydrofuran was added, followed by stirring at room temperature for 16 hours. Subsequently, after refluxing for 2 hours, insolubles were filtered off and the solvent was distilled off. The residue was purified by silica gel column chromatography (solvent: hexane-ethyl acetate=2:1) to give 2 g of (E)-5-phenyl-4-penten-1-ol as a colorless oily substance.

Aufarbeitung

  1. stirringby stirring at room temperature for 16 hours
  2. temperatureSubsequently, after refluxing for 2 hours
  3. filtrationinsolubles were filtered off
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel column chromatography (solvent: hexane-ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-021a769ec5bf44a297e6ddea2e4655b7
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886817

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