Ethyl Acetate → 2-Chloro-5-((4-methoxybenzyl)oxy)pyridine

HRID 2095831Notes

Reaction equation

HRID 2095831 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.C(OCC)(=O)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:21][C:20]2[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 581585042-Chloro-5-((4-methoxybenzyl)oxy)pyridineYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-hydroxypyridine (50 g, 0.386 mol) and potassium carbonate (80 g, 0.579 mol) in N,N-dimethylformamide (300 mL) was added p-methoxybenzyl chloride (66.5 g, 0.425 mol), and the mixture was stirred at 80° C. for 4 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the obtained residue was washed with methanol to give the title compound (61.3 g, 64%) as a white solid.

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washthe obtained residue was washed with methanol

Sources & evidence

ORD record
ord-c4208c233f764110bdabdf07f6708386
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

Loading…