4-Pentyl-(2,3-difluorophenyl)-cyclohexene → 4-Pentyl-(2,3-difluorophenyl)cyclohexane

HRID 1943544Notes

Reaction equation

HRID 1943544 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])=[CH:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H][H]>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 144956434-Pentyl-(2,3-difluorophenyl)-cyclohexeneHCID 178418361HCID 178418361, compound

Product 1

HCID 199109694-Pentyl-(2,3-difluorophenyl)cyclohexaneYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

The compound (9) (50.0 g) was dissolved in a mixed solvent of toluene (150 ml) and Solmix A-11 (150 ml), Pd/C (0.5 g) was added thereto, and the mixture was stirred at room temperature under a hydrogen atmosphere until hydrogen absorption had ceased. After the reaction had been completed, Pd/C was removed and then the solvent was distilled off. The residue obtained was purified with a fractional operation by means of column chromatography using heptane as the eluent and silica gel as the stationary phase powder, and further purified by means of recrystallization from Solmix A-11 and dried, giving 47.0 g of 4-pentyl-(2,3-difluorophenyl)cyclohexane (10). The yield based on the compound (9) was 94.0%.

Workup

  1. additionwas added
  2. customPd/C was removed
  3. distillationthe solvent was distilled off
  4. customThe residue obtained
  5. customwas purified with a fractional operation by means of column chromatography
  6. customfurther purified by means of recrystallization from Solmix A-11
  7. customdried

Sources & evidence

ORD record
ord-91369208061a4f20b5dedd556b31f109
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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