Lithium diisopropylamide → 1-(1-Cyano-3-methylcyclohexyl)-2-(4'-pentylbiphenyl-4-yl)ethane

HRID 231461Notes

Reaction equation

HRID 231461 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]#[N:9])[CH2:3]1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1>C1COCC1>[C:8]([C:4]1([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)[CH2:5][CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3]1)#[N:9]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 198007403-Methylcyclohexane-1-carbonitrileHCID 200326171-Bromo-2-(4'-pentylbiphenyl-4-yl)ethane

Product 1

HCID 200915111-(1-Cyano-3-methylcyclohexyl)-2-(4'-pentylbiphenyl-4-yl)ethane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3.1 g of 3-methylcyclohexanecarbonitrile and 30 ml of THF has added to it at -78° a solution of lithium diisopropylamide (prepared from 3.3 g of diisopropylamine, 30 ml of THF and 19 ml of 1.6-molar butyllithium solution in hexane) and then a solution of 9.7 g of 1-bromo-2-(4'-pentylbiphenyl-4-yl)ethane in 30 ml of THF. Working up as in Example 1 gives 1-(1-cyano-3-methylcyclohexyl)-2-(4'-pentylbiphenyl-4-yl)ethane, m.p. 73°.

Sources & evidence

ORD record
ord-d65c46e3ffae4b9098bf1cbf9c0f73cf
Source dataset
uspto-grants-1989_07
Patent number
US04846998

Reaction notes

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