HCID 54243437, compound → HCID 14278573, compound

HRID 2165983Notes

Reaction equation

HRID 2165983 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=1)=[CH:4][CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1>C(O)C.[Pd]>[F:1][C:2]([F:31])([F:32])[CH:3]([C:20]1[CH:21]=[CH:22][C:23]([O:26][C:27]([F:28])([F:29])[F:30])=[CH:24][CH:25]=1)[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1

Participants

4

Reactant 1

HCID 54243437HCID 54243437, compound

Product 1

HCID 14278573HCID 14278573, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The (2E, 4E) isomer of 1,1,1-trifluoro-2-(4-trifluoromethoxyphenyl)-5-(3-phenoxyphenyl)penta-2,4-diene (2.7 g) in ethanol (80 cm3) in the presence of a hydrogenation catalyst (10% palladium on charcoal, 200 mg) was stirred under an atmosphere of hydrogen at a pressure of 3.7 atmospheres for 1 hour. The reaction mixture was filtered through celite to remove the catalyst and the celite washed with further ethanol. The combined filtrates were concentrated by evaporation of the ethanol under reduced pressure to yield 1,1,1-trifluoro-2-(4-trifluoromethoxyphenyl)-5-(3-phenoxyphenyl)pentane (2.09 g) as a colourless oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customto remove the catalyst
  3. washthe celite washed with further ethanol
  4. concentrationThe combined filtrates were concentrated by evaporation of the ethanol under reduced pressure

Sources & evidence

ORD record
ord-d7ff84eea6b5480eabc59e6aa1858d2c
Source dataset
uspto-grants-1990_07
Patent number
US04942264

Reaction notes

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