Hydrochloric Acid → 1-[3-Chloro-4-(1,3-oxazol-2-yl)phenyl]-4,4,4-trifluoro-1,3-butanedione

HRID 394858Notes

Reaction equation

HRID 394858 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13](=[O:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[C:8]1[O:9][CH:10]=[CH:11][N:12]=1.[F:16][C:17]([F:24])([F:23])[C:18](OCC)=[O:19].C[O-].[Na+].Cl>COC(C)(C)C.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:13](=[O:15])[CH2:14][C:18](=[O:19])[C:17]([F:24])([F:23])[F:16])[CH:5]=[CH:6][C:7]=1[C:8]1[O:9][CH:10]=[CH:11][N:12]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 223138001-[3-Chloro-4-(1,3-oxazol-2-yl)phenyl]-1-ethanone

Product 1

HCID 223138391-[3-Chloro-4-(1,3-oxazol-2-yl)phenyl]-4,4,4-trifluoro-1,3-butanedioneYield 113.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 1-[3-chloro-4-(1,3-oxazol-2-yl)phenyl]-1-ethanone (1.89 g, 8.572 mmol) in t-butyl methyl ether (100 mL) were added ethyl trifluoroacetate (1.1 mL, 9.38 mmol) and 28%wt sodium methoxide in MeOH (2.6 ml) at 0° C. and stirred at room temperature for 4 hours. Water (100 mL) was added to the mixture, the mixture was neutralized with 2N HCl, extracted with ethyl acetate (100 mL×2) and dried over MgSO4. Removal of the solvent, gave a title compound (3.08 g).

Workup

  1. extractionextracted with ethyl acetate (100 mL×2)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-45c4597739ef47e89607dfffac3f3c96
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

Loading…