4-Ethynyl-4,4'-dipentylbicyclohexyl → 4-[4-(4-Methoxy-4'-propylbicyclohexyl-4-yl)buta-1,3-diynyl]-4-methoxy-4'-propylbicyclohexyl

HRID 1532538

Reaktionsgleichung

Reaktionsgleichung von HRID 1532538
[C:1]([C:3]1([O:18][CH3:19])[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)#[CH:2].C(C1(CCCCC)CCC(C2CCC(CCCCC)CC2)CC1)#C.C(C1(C#C[C:68]#[C:69][C:70]2([O:85][CH3:86])[CH2:75][CH2:74][CH:73]([CH:76]3[CH2:81][CH2:80][CH:79]([CH2:82][CH2:83][CH3:84])[CH2:78][CH2:77]3)[CH2:72][CH2:71]2)CCC(C2CCC(CCCCC)CC2)CC1)CCCC>N1C=CC=CC=1.CO.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.[Cu]I>[CH3:19][O:18][C:3]1([C:1]#[C:2][C:68]#[C:69][C:70]2([O:85][CH3:86])[CH2:75][CH2:74][CH:73]([CH:76]3[CH2:81][CH2:80][CH:79]([CH2:82][CH2:83][CH3:84])[CH2:78][CH2:77]3)[CH2:72][CH2:71]2)[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1

Komponenten

8

Edukt 3

HCID 154519764-Ethynyl-4,4'-dipentylbicyclohexylHCID 183645084-Ethynyl-4-methoxy-4'-propylbicyclohexylHCID 220133924-[4-(4,4'-Dipentylbicyclohexyl-4-yl)buta-1,3-diynyl]-4-methoxy-4'-propylbicyclohexyl

Produkt 1

HCID 220133944-[4-(4-Methoxy-4'-propylbicyclohexyl-4-yl)buta-1,3-diynyl]-4-methoxy-4'-propylbicyclohexyl

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 165397Cupric acetate monohydrateKatalysatorHCID 887MethanolLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

4.00 g of 4-ethynyl-4-methoxy-4′-propylbicyclohexyl, 5.04 g of 4-ethynyl-4,4′-dipentylbicyclohexyl, 10.65 g of copper(II) acetate monohydrate and 0.145 g of copper(I) iodide are refluxed overnight in a mixture of 25 ml of pyridine and 25 ml of methanol. Conventional work-up gives a mixture of the three coupling products 4-[4-(4,4′-dipentylbicyclohexyl-4-yl)buta-1,3-diynyl]-4-methoxy-4′-propylbicyclohexyl (C 76 N 136 I, Δε=0.95, Δn=0.006), 4-[4-(4,4′-dipentylbicyclohexyl-4-yl)buta-1,3-diynyl]-4,4′-dipentylbicyclohexyl and 4-[4-(4-methoxy-4′-propylbicyclohexyl-4-yl)buta-1,3-diynyl]-4-methoxy-4′-propylbicyclohexyl (C 121 N (80) I, Δε=−1.77, Δn=−0.002), which can easily be separated by chromatography.

Aufarbeitung

  1. customConventional work-up gives
  2. customcan easily be separated by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ac3ea0183fdc49738a20c64380ee4998
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06203724B1

Verknüpfte Notizen

Wird geladen…