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

HRID 1109418

반응식

HRID 1109418 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 11401075(Z)-4-benzyloxy-2-butenal수율 65.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b7e175674d934e1ba7938e644e4457ae
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05319082

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