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

HRID 374714Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-0f472a61010e4409a2394b4befe611e4
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05481036

Reaction notes

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