HCID 67207151, compound → HCID 58288421, compound

HRID 1476094Notes

Reaction equation

HRID 1476094 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

HCID 67207151HCID 67207151, compound

Product 1

HCID 58288421HCID 58288421, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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).

Workup

  1. filtrationThe mixture was then filtered off through celite
  2. washthe residue was washed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue obtained
  5. customwas purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1)

Sources & evidence

ORD record
ord-49245502d661459bbc5a70822d3bdc9e
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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