Cyclopentadiene → 2,2-Bis(cyclopentadienyl)-5-trimethylsiloxypentane

HRID 1862076

Reaktionsgleichung

Reaktionsgleichung von HRID 1862076
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.C[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:17][Si:18]([CH3:27])([CH3:26])[O:19][CH2:20][CH2:21][CH2:22][C:23](=O)[CH3:24]>C1COCC1>[CH:2]1([C:23]([CH:13]2[CH:12]=[CH:16][CH:15]=[CH:14]2)([CH2:22][CH2:21][CH2:20][O:19][Si:18]([CH3:27])([CH3:26])[CH3:17])[CH3:24])[CH:1]=[CH:5][CH:4]=[CH:3]1

Komponenten

6

Edukt 4

HCID 7612CyclopentadieneHCID 8058HexaneHCID 136099385-Trimethylsiloxypentan-2-oneHCID 178418339Butyllithium

Produkt 1

HCID 120953572,2-Bis(cyclopentadienyl)-5-trimethylsiloxypentaneAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Freshly distilled cyclopentadiene (61.5 g, 0.93 mol) was placed in a one liter Schlenk flask and dissolved in dry THF (500 ml). n-BuLi 2.5 M in hexane (372 ml 0.93 mol) was slowly added to this solution at −78° C., yielding a white precipitate. The suspension was left to reach room temperature and then heated to 65° C. for one hour. The reaction mixture is thermostated at 20° C. and a solution of 5-trimethylsiloxypentan-2-one (72.5 g, 0.42 mol) in THF (100 ml) was slowly added. The yellow suspension obtained was heated at reflux for 16 h. The resulting brown suspension was filtered and the solid washed with hexane several times. Solvents were removed under vacuum and the orange oil obtained was distilled at 10−3 mbar and 84-89° C., obtaining a yellow oil (20.5 g, 17% yield). 1H NMR (CDCl3): Λ6.40-6.02 (C5H5, 6H), 3.55 (CH2, m, 2H), 2.97, 2.80 and 2.78 (C5H5, 4H), 1.82 (CH2, m, 2H), 1.42 (CH2, m, 2H), 1.40 (CH3, s, 3H), 0.10 ((CH3)3, s, 9H).

Aufarbeitung

  1. customyielding a white precipitate
  2. waitThe suspension was left
  3. customto reach room temperature
  4. customat 20° C.
  5. customThe yellow suspension obtained
  6. temperaturewas heated
  7. temperatureat reflux for 16 h
  8. filtrationThe resulting brown suspension was filtered
  9. washthe solid washed with hexane several times
  10. customSolvents were removed under vacuum
  11. customthe orange oil obtained
  12. distillationwas distilled at 10−3 mbar and 84-89° C.

Quellen und Nachweise

ORD-Eintrag
ord-a89e9e117bfc42e8a695d3824d2b425b
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534665B1

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