HCID 58212270, compound → HCID 58212302, compound

HRID 1095258Notes

Reaction equation

HRID 1095258 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH:19]1[CH2:24][CH2:23][CH:22]([CH:25]2[CH2:30][CH2:29][CH:28]([CH:31]=[CH2:32])[CH2:27][CH2:26]2)[CH2:21][CH2:20]1.[H][H]>C1(C)C=CC=CC=1.[Pd]>[CH2:31]([CH:28]1[CH2:27][CH2:26][CH:25]([CH:22]2[CH2:21][CH2:20][CH:19]([C:3]3[CH:4]=[CH:5][C:6]([CH:8]4[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]4)=[CH:7][C:2]=3[F:1])[CH2:24][CH2:23]2)[CH2:30][CH2:29]1)[CH3:32]

Participants

5

Reactant 2

HCID 58212270HCID 58212270, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58212302HCID 58212302, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

4-[2-Fluoro-4-(4-pentylcylohexyl)-phenyl]-4′-vinyl-bicyclohexyl (No. 5) (1.5 g) obtained in Example 1 was dissolved in a mixed solvent of toluene (15 ml) and Solmix (15 ml), and Pd/C (0.20 g) was added thereto. 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 was purified with a fractional operation by means of column chromatography using heptane as an eluent and silica gel as a stationary phase powder, and further purified by means of recrystallization from heptane and dried, giving 0.78 g of 4-ethyl-4′-(2-fluoro-4-(4-pentylcyclohexyl) phenyl) bi (cyclohexane) (E). The yield based on the compound (No. 5) was 51.8%.

Workup

  1. custom5) (1.5 g) obtained in Example 1
  2. additionwas added
  3. customPd/C was removed
  4. distillationthe solvent was distilled off
  5. customThe residue was purified with a fractional operation by means of column chromatography
  6. customsilica gel as a stationary phase powder, and further purified by means of recrystallization from heptane
  7. customdried

Sources & evidence

ORD record
ord-ac6b5f78fffd4272bd5eaaa4ef7fb7b9
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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