Dimethyl Sulfoxide → 4-(1-Ethyl-propoxy)-2-methyl-8-(2,4,6-trimethyl-phenyl)-quinoline

HRID 1813915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1813915
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[C:19]2[C:14](=[C:15]([C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([CH3:29])[CH:11]=1.CS(C)=O>C1COCC1>[CH2:2]([CH:3]([O:6][C:10]1[C:19]2[C:14](=[C:15]([C:20]3[C:21]([CH3:28])=[CH:22][C:23]([CH3:27])=[CH:24][C:25]=3[CH3:26])[CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([CH3:29])[CH:11]=1)[CH2:4][CH3:5])[CH3:1]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 114283-PentanolHCID 24758Sodium hydrideHCID 225043522-Methyl-4-chloro-8-(2,4,6-trimethylphenyl)-quinoline

Produkt 1

HCID 98412214-(1-Ethyl-propoxy)-2-methyl-8-(2,4,6-trimethyl-phenyl)-quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
12 °C

Versuchsvorschrift

To a solution of 3-pentanol (5.8 ml, 52.7 mmol) in dry THF (5 ml) was added sodium hydride (NaH) portionwise over a period of 10 min. A solution of 4-chloro-2-methyl-8-(2,4,6-trimethyl-phenyl)-quinoline (4.0006 g, 13.52 mmol) in dry THF (10 ml) was added. After stirring at room temperature as for 10 min, 15 ml of dry DMSO was added. The resulting mixture was heated in a 12° C. oil bath for 1.5 hours. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, dried, filtered, and concentrated to give the title compound as 5.002 g of a yellow solid.

Aufarbeitung

  1. additionwas added
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cd1a60c919e14cc2af1b0e49b4aed068
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875769B2

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