Water → 1-{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl}-3,3-dimethyl-1-butanone

HRID 228576Notes

Reaction equation

HRID 228576 reaction equation
Br[C:2]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.C([Li])CCC.CCCCCC.[C:35]([CH2:39][C:40](Cl)=[O:41])([CH3:38])([CH3:37])[CH3:36].O>O1CCCC1>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:17][CH3:18])[N:8]=[CH:7][CH:6]=[C:5]2[O:4][C:3]1[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:2]=1[C:40](=[O:41])[CH2:39][C:35]([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 815143,3-Dimethylbutanoyl chlorideHCID 230783624-(2-Bromo-4-methylphenoxy)-6,7-dimethoxyquinolineHCID 178418244HCID 178418244, compound

Product 1

HCID 577565731-{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl}-3,3-dimethyl-1-butanoneYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-(2-Bromo-4-methylphenoxy)-6,7-dimethoxyquinoline (100 mg) was dissolved in tetrahydrofuran (6 ml) to prepare a solution which was then cooled to −78° C. A 1.59 M n-butyllithium/hexane solution (0.4 ml) was added thereto, and the mixture was stirred at −78° C. for 20 min. Tert-butylacetyl chloride (0.2 ml) was added to the reaction solution, and the mixture was stirred at room temperature overnight. Further, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (15 mg, yield 14%).

Workup

  1. customto prepare a solution which
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was then washed with water and saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. distillationby distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-b98517eee7954c81ad0061772a533b7f
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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