HCID 67058748, compound → HCID 23159688, compound

HRID 1174445Notes

Reaction equation

HRID 1174445 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[CH:28]([F:30])[F:29])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]>[C].[Pd]>[F:30][CH:28]([F:29])[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 67058748HCID 67058748, compound

Product 1

HCID 23159688HCID 23159688, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

1.6 g of β-(4-(4-propylcyclohexyl)cyclohexyl)-2-difluoromethyl-3-fluoro-4-ethoxy styrene obtained in Example 5 was dissolved in 25 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 days. 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=9/1) to obtain 1-(2-difluoromethyl-3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane. This was further recrystallized twice from a heptane/ethanol mixed solvent to obtain pure 1-2-difluoromethyl-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=9/1)

Sources & evidence

ORD record
ord-0ea5cd72ae374a11a0baae1b21791a2e
Source dataset
uspto-grants-2010_11
Patent number
US07838087B2

Reaction notes

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