Potassium Carbonate → Ethyl 3(2-ethyl-4-{2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethoxy}phenyl)propionate

HRID 526799Notes

Reaction equation

HRID 526799 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:2].CS(O[CH2:22][CH2:23][C:24]1[N:25]=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[O:27][C:28]=1[CH3:29])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([C:3]1[CH:8]=[C:7]([O:9][CH2:22][CH2:23][C:24]2[N:25]=[C:26]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[O:27][C:28]=2[CH3:29])[CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 225071532-[2-(4-Fluorophenyl)-5-methyloxazol-4-yl]ethyl methanesulfonateHCID 45095457Ethyl 3-(2-ethyl-4-hydroxyphenyl)propanoate

Product 1

HCID 86680651Ethyl 3(2-ethyl-4-{2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethoxy}phenyl)propionate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The parent phenolic compound, ethyl 3-(2-ethyl-4-hydroxylphenyl)propionate (10.4 g, 50 mmol) and 120 ml acetonitrile were added into a 250 ml single neck flask, and stirred. Then the parent sulfonate compound, 2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethyl methanesulfonate (15 g, 50 mmol) and potassium carbonate (K2CO3) (100 mmol) were added. The mixture was heated for 16 hours under reflux. After the reaction was completed, the product was filtered. The filter cake was washed with ethyl acetate (3×50 ml) and then discarded. The filtrates were combined, and the solvent was distilled off under reduced pressure, to obtain crude ethyl 3-(2-ethyl-4-{2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethoxy}phenyl)propionate. The crude ethyl 3-(2-ethyl-4-{2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethoxy}phenyl)propionate, without purification, was dissolved with 120 ml ethanol. 10% NaOH (30 ml) was added at room temperature, and the stirring was maintained for 3 hours at room temperature. After the reaction was completed, the product was acidified by adding 10% dilute hydrochloric acid, to obtain a solid precipitate. It was filtered by suction filtration, to obtain crude 3-(2-ethyl-4-{2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethoxy}phenyl)propionic acid. The crude product was crystallized by ethyl acetate-petroleum ether, to obtain 12.3 g white solid, with a yield of 62% from the 2 steps.

Workup

  1. temperatureThe mixture was heated for 16 hours
  2. temperatureunder reflux
  3. filtrationthe product was filtered
  4. washThe filter cake was washed with ethyl acetate (3×50 ml)
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-237edfa582f644c0a39d7fdd01b6f4cc
Source dataset
uspto-grants-2016_05
Patent number
US09346770B2

Reaction notes

Loading…