HCID 178418361, compound → HCID 178444443, compound

HRID 35787Notes

Reaction equation

HRID 35787 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][CH:14]=[CH:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H][H]>[Pd].C(OCC)(=O)C>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178444442HCID 178444442, compound

Product 1

HCID 178444443HCID 178444443, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 40 g of 4-[4-(trans-4-pentylcyclohexyl)-1-butenyl]benzonitrile, 2 g of palladium/carbon (5%) and 250 ml of ethyl acetate was stirred while gassing with hydrogen. Subsequently, the inorganic material was filtered off and the filtrate was concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from ethanol gave 36 g of pure 4-[4-(trans-4-pentylcyclohexyl)-1-butyl]benzonitrile with m.p. 51° C.

Workup

  1. filtrationSubsequently, the inorganic material was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-19a6607505fa4764af6973fedee4b1df
Source dataset
uspto-grants-1995_05
Patent number
US05411676

Reaction notes

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