HCID 178418361, compound → HCID 178444443, compound

HRID 2371347Notes

Reaction equation

HRID 2371347 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-2a4aaf09c1bc4d6e9cd503d72de97763
Source dataset
uspto-grants-1992_03
Patent number
US05093027

Reaction notes

Loading…