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Selenium Dioxide → 4-formyl-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 25782
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 25782
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[CH:15][CH:16]=2)[C:11]([CH3:26])=[CH:10][C:9]1([CH3:28])[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Se](=O)=[O:30]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[CH:15][CH:16]=2)[C:11]([CH:26]=[O:30])=[CH:10][C:9]1([CH3:28])[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]
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Komponenten

4

Edukt 2

HCID 24007Selenium Dioxide2×HCID 207603346-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 207603334-formyl-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl esterAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 1.6 g of 6-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester, 20 mL of 1,4-dioxane, and 1.4 g of selenium dioxide was refluxed for half an hour. Another 1.4 g portion of selenium dioxide was added. The reaction was allowed to reflux for 6 hours. The reaction mixture was then filtered through diatomaceous earth and the residue was rinsed with EtOAc. The solvent was evaporated in vacuo and the residue was purified by flash chromatography to yield 1 g of 4-formyl-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as a solid.

Aufarbeitung

  1. temperaturewas refluxed for half an hour
  2. temperatureto reflux for 6 hours
  3. filtrationThe reaction mixture was then filtered through diatomaceous earth
  4. washthe residue was rinsed with EtOAc
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c8da3bcdb5624a269111564194fcc524
Quelldatensatz
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06858627B2

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