HCID 13885636, compound → HCID 21282148, compound

HRID 414299Notes

Reaction equation

HRID 414299 reaction equation
C(OC1C=CC(C(CCCC2C=CC=C(OC3C=CC=CC=3)C=2)C(F)(F)F)=CC=1)C.[CH2:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40](=[C:45]([C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([O:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[CH:49]=2)[CH2:46][CH3:47])[C:41]([F:44])([F:43])[F:42])=[CH:36][CH:35]=1)[CH3:32]>C(O)C.[Pd]>[CH2:31]([O:33][C:34]1[CH:35]=[CH:36][C:37]([CH:40]([CH:45]([C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([O:54][C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[CH:49]=2)[CH2:46][CH3:47])[C:41]([F:44])([F:43])[F:42])=[CH:38][CH:39]=1)[CH3:32]

Participants

5

Reactant 2

HCID 13885636HCID 13885636, compoundHCID 54344968HCID 54344968, compound

Product 1

HCID 21282148HCID 21282148, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

This Example illustrates the preparation of 2-(4-ethoxyphenyl)-5-(3-phenoxyphenyl)-1,1,1-trifluoropentane. A mixture of E and Z isomers of 2-(4-ethoxyphenyl)-3-(3-phenoxyphenyl)-1,1,1-trifluoropent-2-ene (0.4 g) in ethanol (20 cm3) in the presence of a hydrogenation catalyst (10% palladium on charcoal, 50 mg) was stirred under an atmosphere of hydrogen at a pressure of 2 atmospheres for 1 hour, then 4 atmospheres for 4 hours. The reaction mixture was filtered to remove the catalyst and the filtrate concentrated by removal of the ethanol by evaporation under reduced pressure. The residue was dissolved in chloroform, and the solution washed with water twice, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent under reduced pressure. The residual oil was purified by column chromatography using a short silica gel column eluted with 2:25 mixture by volume of ethyl acetate and hexane to yield 2-(4-ethoxyphenyl)-3-(3-phenoxyphenyl)-1,1,1-trifluoropentane (0.32 g) as a colourless oil.

Workup

  1. wait4 atmospheres for 4 hours
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationthe filtrate concentrated by removal of the ethanol by evaporation under reduced pressure
  5. dissolutionThe residue was dissolved in chloroform
  6. washthe solution washed with water twice
  7. dry with materialdried over anhydrous magnesium sulphate
  8. concentrationconcentrated by evaporation of the solvent under reduced pressure
  9. customThe residual oil was purified by column chromatography
  10. washeluted with 2:25 mixture by volume of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a14b772f4cfc4d71acd4a804dc43dd93
Source dataset
uspto-grants-1988_12
Patent number
US04791139

Reaction notes

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