Pyridine → 4-[4-(4,4'-Dipentylbicyclohexyl-4-yl)buta-1,3-diynyl]-4,4'-dipentylbicyclohexyl

HRID 1532535Notes

Reaction equation

HRID 1532535 reaction equation
[C:1]([C:3]1([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)#[CH:2].N1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CO>[CH2:1]([C:3]1([C:20]#[C:21][C:22]#[C:23][C:24]2([CH2:11][CH2:10][CH2:9][CH2:14][CH3:13])[CH2:30][CH2:29][CH:28]([CH:6]3[CH2:7][CH2:8][CH:3]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:4][CH2:5]3)[CH2:27][CH2:26]2)[CH2:4][CH2:5][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]2)[CH2:7][CH2:8]1)[CH2:2][CH2:16][CH2:15][CH3:12]

Participants

5

Reactant 2

HCID 1049PyridineHCID 154519764-Ethynyl-4,4'-dipentylbicyclohexyl

Product 1

HCID 154568264-[4-(4,4'-Dipentylbicyclohexyl-4-yl)buta-1,3-diynyl]-4,4'-dipentylbicyclohexyl

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5.00 g of 4-ethynyl-4,4′-dipentylbicyclohexyl, 12.5 ml of pyridine, 12.5 ml of methanol and 3.635 g of copper(II) acetate monohydrate is stirred at RT for 1.5 hours and subsequently heated at the boil. The mixture is stirred for 10 hours and subjected to conventional work-up, giving 4-[4-(4,4′-dipentylbicyclohexyl-4-yl)buta-1,3-diynyl]-4,4′-dipentylbicyclohexyl (C 77 SmB 198 I, Δn=0.013, Δε=−0.27).

Workup

  1. temperaturesubsequently heated at the boil
  2. stirringThe mixture is stirred for 10 hours

Sources & evidence

ORD record
ord-4e45b047afad49e6bf135be39e3ff85e
Source dataset
uspto-grants-2001_03
Patent number
US06203724B1

Reaction notes

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