Hydrochloric Acid → 4,4,4-Trifluoro-1-(3-fluoro-4-(1,3-thiazol-4-yl)phenyl)-1,3-butanedione

HRID 2086676Notes

Reaction equation

HRID 2086676 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13](=[O:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[CH:10][S:11][CH:12]=1.[F:16][C:17]([F:24])([F:23])[C:18](OCC)=[O:19].C[O-].[Na+].Cl>C(OC)(C)(C)C>[F:16][C:17]([F:24])([F:23])[C:18](=[O:19])[CH2:14][C:13]([C:4]1[CH:5]=[CH:6][C:7]([C:8]2[N:9]=[CH:10][S:11][CH:12]=2)=[C:2]([F:1])[CH:3]=1)=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 223138303-Fluoro-4-(1,3-thiazol-4-yl)phenyl-1-ethanone

Product 1

HCID 223138014,4,4-Trifluoro-1-(3-fluoro-4-(1,3-thiazol-4-yl)phenyl)-1,3-butanedioneYield 99%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a stirred solution of 1-[3-fluoro-4-(1,3-thiazol-4-yl)phenyl]-1-ethanone (666 mg, 3.01 mmol), ethyl trifluoroacetate (470 mg, 3.31 mmol) in t-butylmethylether (40 ml) was added sodium methoxide (28 wt. % solution in methanol; 0.8 ml, 3.6 mmol) over 5 minutes, and the mixture was stirred for 20 hours. The mixture was made neutral by addition of 2N HCl aqueous solution, and the whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was used for next reaction without purification. (1.06 g, 99% yield).

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was used for next reaction without purification

Sources & evidence

ORD record
ord-b59266b644764c85b2aebe737701eb13
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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