HCID 178418361, compound → HCID 178442086, compound

HRID 370699Notes

Reaction equation

HRID 370699 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:5][CH2:4]1)#[N:2].[H][H]>C1(C)C=CC=CC=1.C(O)C.[Pd]>[C:1]([C@H:3]1[CH2:4][CH2:5][C@H:6]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)[CH2:7][CH2:8]1)#[N:2]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178442085HCID 178442085, compound

Product 1

HCID 178442086HCID 178442086, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21863594Toluene ethanolSolvent

Procedure

3.4 g of 4-[2-(trans-4-cyanocyclohexyl)ethenyl]-4'-pentylbiphenyl were dissolved in 150 ml of toluene/ethanol (volume ratio 4:1), treated with 300 ml of 10% palladium/carbon and hydrogenated at normal pressure and room temperature until the hydrogen uptake came to a standstill. Filtration of the mixture and low-pressure chromatography (0.5 bar) of the concentrated filtrate on silica gel with 5% ethyl acetate/petroleum ether as the eluant gave 3.08 g of 4-[2-(trans-4-cyanocyclohexyl)-ethyl]-4'-pentylbiphenyl as colourless crystals (purity 99.2%; yield 86% based on trans-4-cyanocyclohexanecarboxaldehyde). By additional recrystallization of a sample from ethanol there was obtained pure product of melting point (C-S) 59.7° C., t.p. (S-S) 68.1° C., t.p. (S-N) 89.0° C. and cl.p. (N-I) 134.5° C.

Workup

  1. filtrationFiltration of the mixture and low-pressure chromatography (0.5 bar) of the concentrated filtrate on silica gel with 5% ethyl acetate/petroleum ether as the eluant

Sources & evidence

ORD record
ord-1818ff91c3ad4c9e8460809c90ad8c50
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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