HCID 178447878, compound → HCID 178448066, compound

HRID 395935Notes

Reaction equation

HRID 395935 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH:10]2[CH2:15][CH2:14][C:13]([C:16]([F:28])([F:27])[O:17][C:18]3[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]([F:26])[CH:19]=3)=[CH:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]>C1(C)C=CC=CC=1.C(O)C.[C].[Pd]>[CH2:1]([C@H:4]1[CH2:5][CH2:6][C@H:7]([C@H:10]2[CH2:11][CH2:12][C@H:13]([C:16]([F:27])([F:28])[O:17][C:18]3[CH:19]=[C:20]([F:26])[C:21]([F:25])=[C:22]([F:24])[CH:23]=3)[CH2:14][CH2:15]2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 178447878HCID 178447878, compound

Product 1

HCID 178448066HCID 178448066, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

In a nitrogen-purged 1-L stainless steel autoclave, 7.3 g (18.1 mmol) of 1-(4-(trans-4-propylcyclohexyl)cyclohexene-1-yl-difluoromethoxy)-3,4,5-trifluorobenzene obtained in the second step was dissolved in 250 ml of a mixed solution of equal amount of toluene/ethanol. 0.6 g of 5% palladium carbon catalyst was added thereto, and the mixture was stirred at room temperature under a hydrogen pressure of 0.8 MPa for 5 hours. The catalyst was separated from the reaction mixture by filtration, and then the solvent was distilled off under reduced pressure. The concentrated residue was purified by means of a silica gel column chromatography with heptane as a developing solvent and further recrystallized from a mixed solution of equal amount of heptane/ethanol to obtain 5.1 g of 1-(trans-4-(trans-4-propylcyclohexyl)-cyclohexyldifluoromethoxy)-3,4,5-trifluorobenzene as colorless crystals.

Workup

  1. customobtained in the second step
  2. customThe catalyst was separated from the reaction mixture by filtration
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe concentrated residue was purified by means of a silica gel column chromatography with heptane as a developing solvent
  5. customfurther recrystallized from a mixed solution of equal amount of heptane/ethanol

Sources & evidence

ORD record
ord-8775e654f8a6413a9feede834a710b3a
Source dataset
uspto-grants-2003_08
Patent number
US06605747B2

Reaction notes

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