p-Toluenesulphonyl cyanide → 4-Cyanoethynyl-4'-propylbicyclohexyl-4-yl 4-propylcyclohexanecarboxylate

HRID 380259Notes

Reaction equation

HRID 380259 reaction equation
[CH:1]([N-:4]C(C)C)(C)C.[Li+].[CH2:9]([CH:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20][C:21]2([C:36]#[CH:37])[CH2:26][CH2:25][CH:24]([CH:27]3[CH2:32][CH2:31][CH:30]([CH2:33][CH2:34][CH3:35])[CH2:29][CH2:28]3)[CH2:23][CH2:22]2)=[O:19])[CH2:14][CH2:13]1)[CH2:10][CH3:11].C1(C)C=CC(S(C#N)(=O)=O)=CC=1>C1COCC1>[CH2:9]([CH:12]1[CH2:13][CH2:14][CH:15]([C:18]([O:20][C:21]2([C:36]#[C:37][C:1]#[N:4])[CH2:26][CH2:25][CH:24]([CH:27]3[CH2:28][CH2:29][CH:30]([CH2:33][CH2:34][CH3:35])[CH2:31][CH2:32]3)[CH2:23][CH2:22]2)=[O:19])[CH2:16][CH2:17]1)[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 87946p-Toluenesulphonyl cyanideHCID 2724682Lithium diisopropylamideHCID 183645094-Ethynyl-4'-propylbicyclohexyl-4-yl 4-propylcyclohexanecarboxylate

Product 1

HCID 183645064-Cyanoethynyl-4'-propylbicyclohexyl-4-yl 4-propylcyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

5.10 ml of a 26% solution of lithium diisopropylamide in THF are added dropwise at −70° C. to 4.00 g of 4-ethynyl-4′-propylbicyclohexyl-4-yl 4-propylcyclohexanecarboxylate in 30 ml of THF, and the mixture is stirred for 15 minutes. A solution of 1.89 g of p-toluenesulfonyl cyanide in 10 ml of THF is subsequently added dropwise to the reaction solution at this temperature, and the cooling is removed. Conventional work-up gives 4-cyanoethynyl-4′-propylbicyclohexyl-4-yl 4-propylcyclohexanecarboxylate (C 89 N (58) I, Δε−10.18, Δn 0.02).

Workup

  1. customthe cooling is removed

Sources & evidence

ORD record
ord-8c588e1bc32e4ed6a1d4d2f5fd5a60a4
Source dataset
uspto-grants-2001_10
Patent number
US06303194B1

Reaction notes

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