Potassium Carbonate → 3-[4-(2-Benzofuranyl)thiazol-2-yl]propionic acid

HRID 2269708Notes

Reaction equation

HRID 2269708 reaction equation
[OH-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[C:4]1[C:12]1[N:13]=[C:14]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])[S:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[C:4]1[C:12]1[N:13]=[C:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[S:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 18333015Ethyl 3-[4-(2-benzofuranyl)thiazol-2-yl]propionate

Product 1

HCID 183330873-[4-(2-Benzofuranyl)thiazol-2-yl]propionic acidYield 73.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1N Sodium hydroxide (3 ml) was added dropwise to a methanol solution (3 ml) of ethyl 3-[4-(2-benzofuranyl)thiazol-2-yl]propionate (460 mg) under ice-cooling. The reaction mixture was stirred at room temperature overnight, to which was added 10% aqueous potassium carbonate solution (10 ml), and the mixture was washed with ethyl acetate. The aqueous layer was made acidic (pH 3) by adding 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried and concentrated to obtain the entitled compound (306 mg).

Workup

  1. temperaturecooling
  2. washthe mixture was washed with ethyl acetate
  3. additionby adding 1N hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6535890dff4a4e68984c103596038338
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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