Potassium Carbonate → Ethyl 2-[4-(2-thiazolyloxy)phenyl]propionate

HRID 1678870Notes

Reaction equation

HRID 1678870 reaction equation
Cl[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[O:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 764292-ChlorothiazoleHCID 12785115Ethyl 2-(4-hydroxyphenyl)propanoate

Product 1

HCID 12785117Ethyl 2-[4-(2-thiazolyloxy)phenyl]propionateYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chlorothiazole (5.0 g), ethyl 2-(4-hydroxyphenyl)propionate (8.1 g), potassium carbonate powder (8.65 g) and dimethylformamide (80 ml) is stirred at 150°-155° C for 2.5 hours. The solvent is distilled out under reduced pressure. To the residue is added water and extracted with ether. The extract is washed with a 10% aqueous solution of sodium hydroxide and water and dried. The ether is evaporated. The residue is subjected to chromatography using silica gel and eluted with 50% benzene-hexane, benzene and 10% ether-benzene to yield ethyl 2-[4-(2-thiazolyloxy)phenyl]propionate (5.8 g.). IR νmaxCCl4 1740, 1240, 700 cm-1.

Workup

  1. distillationThe solvent is distilled out under reduced pressure
  2. additionTo the residue is added water
  3. extractionextracted with ether
  4. washThe extract is washed with a 10% aqueous solution of sodium hydroxide and water
  5. customdried
  6. customThe ether is evaporated
  7. washeluted with 50% benzene-hexane, benzene and 10% ether-benzene

Sources & evidence

ORD record
ord-93ebf5c78c5e4d95a87c6b5a02a51429
Source dataset
uspto-grants-1978_03
Patent number
US04077968

Reaction notes

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