1-Bromopropane → 4-(4-Cyano-4-propylcyclohexyl)-4'-pentylbiphenyl

HRID 704282Notes

Reaction equation

HRID 704282 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)#[N:7].BrC1C=CC(C2C=CC(CCCCC)=CC=2)=CC=1.C(NC(C)C)(C)C.BrCCC>CCCCCC.C1COCC1>[C:6]([C:8]1([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)#[N:7]

Participants

8

Reactant 5

HCID 78401-BromopropaneHCID 7912DiisopropylamineHCID 6187094-Bromo-4'-pentylbiphenylHCID 135612464-(4-Cyanocyclohexyl)-4'-pentylbiphenylHCID 178418339Butyllithium

Product 1

HCID 135612474-(4-Cyano-4-propylcyclohexyl)-4'-pentylbiphenyl

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

62.5 ml (0.1 mole) of a 1.6M solution of n-butyl-lithium in hexane and 33.1 g (0.1 mole) of 4-(4-cyanocyclohexyl)-4'-pentylbiphenyl (obtainable by Grignard reaction of 4-bromo-4'-pentyl-biphenyl with 4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-cyclohexanone (J. Org. Chem. 39 (18), 2787-93 (1974)), detachment of water and simultaneous removal of the oxazolyl protective group by boiling with ethanolic H2SO4, hydrogenation of the double bond and subsequent conversion of the ester into the nitrile) in 40 ml of THF are successively added dropwise to 10.1 g (0.1 mole) of diisopropylamine in 70 ml of THF at -10°, with exclusion of moisture and under a nitrogen atmosphere. The reaction mixture is then stirred for 20 minutes. 13.5 g (0.11 mole) of 1-bromopropane are then added, also at -10°, and the mixture is subsequently stirred at room temperature for a further 20 minutes. After customary working up, 4-(4-cyano-4-propylcyclohexyl)-4'-pentylbiphenyl is obtained.

Workup

  1. customwith 4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-cyclohexanone (J. Org. Chem. 39 (18), 2787-93 (1974)), detachment of water and simultaneous removal of the oxazolyl protective group
  2. stirringthe mixture is subsequently stirred at room temperature for a further 20 minutes

Sources & evidence

ORD record
ord-8f80031332e7491b8be4a95b1288ecdb
Source dataset
uspto-grants-1991_01
Patent number
US04985583

Reaction notes

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