Ethyl bromopyruvate → Ethyl 2-(2,2,2-trifluoroethyl)thiazole-4-carboxylate
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.