Butanoic acid, 4-chloro-4-oxo-, ethyl ester → Ethyl 4-(2-thiazolyl)-4-oxobutyrate

HRID 895577Notes

Reaction equation

HRID 895577 reaction equation
C[Si](C)(C)[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.[CH2:10]([O:12][C:13](=[O:19])[CH2:14][CH2:15][C:16](Cl)=[O:17])[CH3:11].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:10]([O:12][C:13](=[O:19])[CH2:14][CH2:15][C:16](=[O:17])[C:3]1[S:4][CH:5]=[CH:6][N:7]=1)[CH3:11]

Participants

5

Reactant 3

HCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 516892Sodium BicarbonateHCID 5884532-Trimethylsilylthiazole

Product 1

HCID 68499389Ethyl 4-(2-thiazolyl)-4-oxobutyrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-trimethylsilanyl-thiazole (2.6 g, 16.53 mmol) in DCM (30 mL) is added a solution of 3-chlorocarbonyl-propionic acid ethyl ester (5.4 g, 32.81 mmol) in DCM (10 mL). The mixture is stirred overnight at room temperature. To the mixture is added 5% NaHCO3 (30 mL) and mixture is stirred at room temperature for 20 minutes. The organic layer is separated and the aqueous lay is extracted with DCM (2×50 mL). The combined organic layers are dried and the solvent removed. The residue is separated by column (methylene chloride) to give 4-oxo-4-thiazol-2-yl-butyric acid ethyl ester.

Workup

  1. stirringis stirred at room temperature for 20 minutes
  2. customThe organic layer is separated
  3. extractionthe aqueous lay is extracted with DCM (2×50 mL)
  4. customThe combined organic layers are dried
  5. customthe solvent removed
  6. customThe residue is separated by column (methylene chloride)

Sources & evidence

ORD record
ord-12d7da43f945484daa8062389421f2d0
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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