Ethyl bromopyruvate → Ethyl 2-(2,2,2-trifluoroethyl)thiazole-4-carboxylate

HRID 471141Notes

Reaction equation

HRID 471141 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](=[S:6])[NH2:5].Br[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C1COCC1>[F:1][C:2]([F:8])([F:7])[CH2:3][C:4]1[S:6][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:5]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 222204183,3,3-Trifluoropropanethioamide

Product 1

HCID 57989344Ethyl 2-(2,2,2-trifluoroethyl)thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,3,3-trifluoropropanethioamide (example 67, step b) (4 g) and ethyl 3-bromo-2-oxopropanoate (5.45 g) in THF (120 mL) was heated at reflux for 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 17% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.9 g.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by flash silica chromatography
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-44281038883f440fb10280b3b0bd8f0b
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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