tert-Butanol → Ethyl 4-methyl-2-(trifluoromethyl)thiazole-5-carboxylate

HRID 591501

Reaction equation

HRID 591501 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](=[S:5])[NH2:4].CC(O)(C)C.Cl[CH:14]([C:20](=O)[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>CCOC(C)=O>[CH3:21][C:20]1[N:4]=[C:3]([C:2]([F:7])([F:6])[F:1])[S:5][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 11858Ethyl 2-chloroacetoacetateHCID 4425751Trifluoroethanethioamide

Product 1

HCID 46835627Ethyl 4-methyl-2-(trifluoromethyl)thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2,2,2-trifluoroethanethioamide (200 mg) and t-BuOH (10 mL) was added ethyl 2-chloro-3-oxobutanoate (0.217 mL) at room temperature. The mixture was refluxed for 2 days. After cooling, EtOAc was poured into the mixture, and the mixture was washed successively with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (NH, EtOAc/hexane) to give the title compound (133 mg).

Workup

  1. temperatureThe mixture was refluxed for 2 days
  2. temperatureAfter cooling
  3. washthe mixture was washed successively with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (NH, EtOAc/hexane)

Sources & evidence

ORD record
ord-efea65c911b44c3f9e75c2d061f7696b
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Linked notes

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