HCID 178444501, compound → HCID 178444502, compound

HRID 395937Notes

Reaction equation

HRID 395937 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH:18]=[CH:19][C:20]([F:32])([F:31])[O:21][C:22]3[CH:27]=[C:26]([F:28])[C:25]([F:29])=[C:24]([F:30])[CH:23]=3)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]>C1(C)C=CC=CC=1.C(O)C.[C].[Pd]>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][C:20]([F:32])([F:31])[O:21][C:22]3[CH:27]=[C:26]([F:28])[C:25]([F:29])=[C:24]([F:30])[CH:23]=3)[CH2:14][CH2:13]2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 178444501HCID 178444501, compound

Product 1

HCID 178444502HCID 178444502, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

In a nitrogen-purged 1-L stainless steel autoclave, 7.7 g (16.8 mmol) of 1-(3-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-1,1-difluoro-2-propenyloxy)-3,4,5-trifluorobenzene obtained in Example 3 was dissolved in 200 ml of a mixed solution of equal amount of toluene/ethanol. 0.8 g of 5% palladium carbon catalyst was added thereto, and the mixture was stirred at room temperature under a hydrogen pressure of 0.1 to 0.2 MPa for 10 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 4.9 g of 1-(3-(trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl)-1,1-difluoropropoxy)-3,4,5-trifluorobenzene as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-67a6f9cb85a543e9bce0400d8f7acf8f
Source dataset
uspto-grants-2003_08
Patent number
US06605747B2

Reaction notes

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