Potassium Carbonate → Methyl 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionate

HRID 359647Notes

Reaction equation

HRID 359647 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:16])[C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:34][O:35][C:36](=[O:40])[C@H:37]([CH3:39])O>CS(C)=O>[CH3:34][O:35][C:36](=[O:40])[CH:37]([O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:5]2[C:4]([F:16])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[CH:14][CH:13]=1)[CH3:39]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 155928384-((5-Chloro-3-fluoro-2-pyridinyl)oxy)phenolHCID 86743051HCID 86743051, compound

Product 1

HCID 15592836Methyl 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 24 g (0.1 mol) of 4-(5-chloro-3-fluoropyridin-2-yloxy)-phenol in 80 ml of dimethylsulfoxide is added dropwise to a stirred solution of 13.8 g (0.1 mol) of potassium carbonate in 50 ml of dimethylsulfoxide. When everything is added, the mixture is stirred for 2 hours at room temperature and then a solution of 25.8 g (0.1 mol) of (S)(-)-lactic acid-methylester tosylate is added dropwise over 30 minutes. The mixture is heated to 60° and stirred at that temperature for 20 hours, then poured onto ice/water and the organic material is extracted three times with ether. The ether-layer is washed with water and saturated salt solution, dried over magnesium sulfate, filtered and evaporated. The residue is passed for purification through a silicagel column with a hexane/ethyl acetate 3:1 solvent. After distillation of the solvent, 26 g of a clear oil of the above ester is obtained ([α]D20 =+38.8°±0.5°2% in acetone).

Workup

  1. additionWhen everything is added
  2. temperatureThe mixture is heated to 60°
  3. stirringstirred at that temperature for 20 hours
  4. additionpoured onto ice/water
  5. extractionthe organic material is extracted three times with ether
  6. washThe ether-layer is washed with water and saturated salt solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is passed for purification through a silicagel column with a hexane/ethyl acetate 3:1 solvent
  11. distillationAfter distillation of the solvent, 26 g of a clear oil of the above ester
  12. customis obtained ([α]D20 =+38.8°±0.5°2% in acetone)

Sources & evidence

ORD record
ord-fd1ec0fc73ff4648965ed97125f64424
Source dataset
uspto-grants-1991_03
Patent number
US05002604

Reaction notes

Loading…