(1s,4r)-4-Propylcyclohexane-1-carboxylic acid → HCID 22013395, compound

HRID 1532541Notes

Reaction equation

HRID 1532541 reaction equation
[CH2:1]([C:6]1([C:23]#[C:24][C:25]2([OH:36])[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:27][CH2:26]2)[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:37]([CH:40]1[CH2:45][CH2:44][CH:43]([C:46](O)=[O:47])[CH2:42][CH2:41]1)[CH2:38][CH3:39]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:37]([CH:40]1[CH2:45][CH2:44][CH:43]([C:46]([O:36][C:25]2([C:24]#[C:23][C:6]3([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10][CH:9]([CH:12]4[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]4)[CH2:8][CH2:7]3)[CH2:26][CH2:27][CH:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:29][CH2:30]2)=[O:47])[CH2:42][CH2:41]1)[CH2:38][CH3:39]

Participants

5

Reactant 2

HCID 1490324(1s,4r)-4-Propylcyclohexane-1-carboxylic acidHCID 22013391HCID 22013391, compound

Product 1

HCID 22013395HCID 22013395, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1.10 g of 1-(4,4′-dipentylbicyclohexyl-4-ylethynyl)-4-pentylcyclohexanol and 0.394 g of 4-propylcyclohexanecarboxylic acid are dissolved in 4 ml of dichloromethane, and 0.283 g of 4-(dimethylamino)pyridine is added. 5.569 g of N,N-dicyclohexylcarbodiimide dissolved in 3 ml of dichloromethane are then added dropwise to the reaction mixture. The mixture is stirred overnight and subjected to conventional work-up, giving 1-(4,4′-dipentylbicyclohexyl-4-ylethynyl)-4-pentylcyclohexyl 4-propylcyclohexanecarboxylate (C 66 SmB 171 I, Δε −0.02).

Workup

  1. additionare then added dropwise to the reaction mixture

Sources & evidence

ORD record
ord-73158d3d5cb544f5bda894cf448e857c
Source dataset
uspto-grants-2001_03
Patent number
US06203724B1

Reaction notes

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