HCID 67207151, compound → HCID 58288421, compound
Reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([N+:17]([O-])=O)[CH:11]=1)=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]>C(O)C.[Pd]>[NH2:17][C:12]1[CH:11]=[C:10]([CH:3]([C:2]([F:21])([F:1])[F:20])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:15]=[CH:14][C:13]=1[F:16]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
5.0 g (16.3 mmol) of ethyl 4,4,4-trifluoro-3-(4-fluoro-3-nitrophenyl)but-2-enoate were dissolved in 133 ml of ethanol, and 866 mg of palladium on carbon (10%) were added under argon. At RT, the reaction mixture was stirred vigorously under an atmosphere of hydrogen (atmospheric pressure) overnight. The mixture was then filtered off through celite and the residue was washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue obtained was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1). This gave 3.91 g of the target product (85.9% of theory).