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

HRID 21553

反応式

HRID 21553 の反応式
[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

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 11008492cis-4-Benzyloxy-2-buten-1-olHCID 178418287HCID 178418287、化合物

生成物 1

HCID 11401075(Z)-4-benzyloxy-2-butenal収率 65.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b1c06dfe898c48e38dc12d83f43513b7
出典データセット
uspto-grants-1995_06
特許番号
US05424309

関連ノート

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