beta-(4-(4-Propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy styrene → 1-(2-Trifluoromethyl-3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane

HRID 1174448Notes

Reaction equation

HRID 1174448 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([CH:16]=[CH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH3:26])=[C:20]([F:27])[C:19]=3[C:28]([F:31])([F:30])[F:29])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]>[C].[Pd]>[F:31][C:28]([F:29])([F:30])[C:19]1[C:20]([F:27])=[C:21]([O:24][CH2:25][CH3:26])[CH:22]=[CH:23][C:18]=1[CH2:17][CH2:16][CH:13]1[CH2:14][CH2:15][CH:10]([CH:7]2[CH2:6][CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8]2)[CH2:11][CH2:12]1

Participants

3

Reactant 1

HCID 67058734beta-(4-(4-Propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy styrene

Product 1

HCID 231597101-(2-Trifluoromethyl-3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

7.89 g of β-(4-(4-propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy styrene obtained in Example 7 was dissolved in 200 ml of a mixed toluene-solmix solvent. A palladium carbon catalyst was added to the solution in a nitrogen atmosphere and a hydrogenation reaction was conducted at ambient temperature and pressure for 2 hours. After the completion of the reaction, the catalyst was removed by filtration. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (eluent: heptane:toluene=4:1) to obtained 1-(2-trifluoromethyl-3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane. This was further recrystallized twice from a heptane/ethanol mixed solvent to obtain 5.35 g of pure 1-(2-trifluoromethyl-3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane. The compound showed a liquid crystal phase and the transition point was as described below.

Workup

  1. customa hydrogenation reaction
  2. customwas conducted at ambient temperature
  3. customAfter the completion of the reaction
  4. customthe catalyst was removed by filtration
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: heptane:toluene=4:1)

Sources & evidence

ORD record
ord-31a3d1c1af6042848d45e85f620a04c5
Source dataset
uspto-grants-2010_11
Patent number
US07838087B2

Reaction notes

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