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Diethyl Ether → 1-(Methyl)-1-(3-butenyl)-1-(cyclopentadienyl)-1-(2,7-di-tert-butylfluorenyl)methane

HRID 604960
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 604960
[CH:1]([C:5]([CH3:11])=[C:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1)=[CH:2][CH2:3][CH3:4].CCOCC.[C:17]([C:21]1[CH:33]=[CH:32][C:31]2[C:30]3[C:25](=[CH:26][C:27]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:28][CH:29]=3)[CH2:24][C:23]=2[C:22]=1[Li])([CH3:20])([CH3:19])[CH3:18].C1C(=C)C=CC=1>CCCCC>[CH3:11][C:5]([CH2:1][CH2:2][CH:3]=[CH2:4])([CH:6]1[CH:7]=[CH:8][CH:9]=[CH:10]1)[C:33]1[C:32]2[CH2:24][C:25]3[C:30](=[CH:29][CH:28]=[C:27]([C:34]([CH3:35])([CH3:36])[CH3:37])[CH:26]=3)[C:31]=2[CH:23]=[CH:22][C:21]=1[C:17]([CH3:19])([CH3:18])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 136323FulveneHCID 540533226-Butenyl-6-methylfulveneHCID 178506710HCID 178506710, Verbindung

Produkt 1

HCID 1317264761-(Methyl)-1-(3-butenyl)-1-(cyclopentadienyl)-1-(2,7-di-tert-butylfluorenyl)methane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8003
Pentane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Another one-liter flask fitted with an addition funnel is charged with 6-butenyl-6-methylfulvene (37 g, 253 mmol) and a stir bar, and cooled to 0° C. under a nitrogen atmosphere. The ether solution of 2,7-di-tert-butylfluorenyl lithium prepared as above is added in a dropwise fashion to the fulvene at 0° C. via the addition funnel over the course of approximately one hour. The resulting dark-colored reaction mixture is warmed to room temperature and stirred overnight (at least about 12 hours) under a nitrogen atmosphere. The reaction mixture is then quenched with the slow addition of a saturated NH4Cl/H2O solution (300 mL), the organic layer extracted with ether, washed twice with H2O (500 mL), dried over anhydrous Na2SO4, filtered, and the filtrate evaporated to dryness. The crude product obtained by this method is then dissolved in pentane and maintained at about 0° C. in a freezer, thereby affording the product as a white solid that is washed with cold pentane, dried under vacuum, and isolated and used without further purification. Further product could be isolated in smaller quantities through concentrating the mother liquors and combined washings and placing them back in freezer.

Aufarbeitung

  1. customAnother one-liter flask fitted with an addition funnel
  2. temperatureThe resulting dark-colored reaction mixture is warmed to room temperature
  3. customThe reaction mixture is then quenched with the slow addition of a saturated NH4Cl/H2O solution (300 mL)
  4. extractionthe organic layer extracted with ether
  5. washwashed twice with H2O (500 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customthe filtrate evaporated to dryness
  9. customThe crude product obtained by this method
  10. temperaturemaintained at about 0° C. in a freezer

Quellen und Nachweise

ORD-Eintrag
ord-8b843dd7445e4ad7b5c4ea52256734f9
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07910763B2

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