Diethyl Ether → (Z)-4-benzyloxy-2-butenal

HRID 1109418

Reaktionsgleichung

Reaktionsgleichung von HRID 1109418
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([O:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][OH:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)C>ClCCl>[CH2:12]([O:19][CH2:20]/[CH:21]=[CH:22]\[CH:23]=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 11008492cis-4-Benzyloxy-2-buten-1-olHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 11401075(Z)-4-benzyloxy-2-butenalAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

11.1 g of pyridinium chlorochromate and 12 g of celite were suspended in 100 ml of dry dichloromethane, and 6 g of (Z)-4-benzyloxy-2-buten-1-ol was added thereto under stirring at 0° C. The mixture was stirred at room temperature for three hours, and then diethyl ether was added thereto. The insolubles were removed by filtration. The filtrate was subjected to distillation under reduced pressure for removal of the solvent, and the residue was purified by silica gel column chromatography (diethyl ether) to obtain 3.9 g of (Z)-4-benzyloxy-butenal as slightly yellow oily substance.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for three hours
  2. customThe insolubles were removed by filtration
  3. distillationThe filtrate was subjected to distillation under reduced pressure for removal of the solvent
  4. customthe residue was purified by silica gel column chromatography (diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-b7e175674d934e1ba7938e644e4457ae
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05319082

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