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

HRID 21553

Reaktionsgleichung

Reaktionsgleichung von HRID 21553
[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 at 0° C. under stirring. The mixture was stirred at room temperature for 3 hours. Diethyl ether was added thereto, and insolubles were removed by filtration. The filtrate was distilled under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (diethyl ether) to obtain 3.9 g of (Z)-4-benzyloxy-2-butenal as slightly yellow oily substance.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. custominsolubles were removed by filtration
  3. distillationThe filtrate was distilled under reduced pressure
  4. customto remove the solvent
  5. customthe residue was purified by silica gel column chromatography (diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-b1c06dfe898c48e38dc12d83f43513b7
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424309

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