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

HRID 1813915Notes

Reaction equation

HRID 1813915 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
12 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cd1a60c919e14cc2af1b0e49b4aed068
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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