Water → HCID 68829194, compound

HRID 228561Notes

Reaction equation

HRID 228561 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][CH:12]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:25]([Mg]Br)[CH3:26].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][CH:12]=2)=[C:6]([CH:7]([OH:8])[CH2:25][CH3:26])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 866051785-Chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]benzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 68829194HCID 68829194, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]benzaldehyde was dissolved in anhydrous tetrahydrofuran (1 ml) to prepare a solution. A 1 M tetrahydrofuran solution (0.5 ml) of ethylmagnesium bromide was added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. Water (1 ml) was added dropwise to the reaction solution to stop the reaction. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure to give 1-{5-chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-1-propanol.

Workup

  1. customto prepare a solution
  2. customthe reaction
  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 by distillation under the reduced pressure

Sources & evidence

ORD record
ord-638dec6f4ffc4b10869233076299bcfc
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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