Water → [1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzene

HRID 2226688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226688
[Li][C@H]1CC(C(O)=O)N([Li])C1=O.[Li]CCCC.[CH3:17][C:18]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[C:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.O>CCOCC.CCCCCC>[CH:19]1([CH:18]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH3:17])[CH:23]=[CH:22][CH:21]=[CH:20]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 5928226-Methyl-6-phenylfulveneHCID 178418339ButyllithiumHCID 178506840HCID 178506840, Verbindung

Produkt 1

HCID 12445303[1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzeneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 0.77 mL of dilithio (s)-(-)-2-pyrrolidone-5-carboxylic acid (6 mmol) in 40 mL of ether was added 7.8 mL of n-BuLi (1.6M solution in hexanes, 13 mmol) at 0° C. This solution was stirred for 30 min at room temperature. The solvent was removed under vacuum and 25 mL of hexane added. 6-Methyl-6-phenylfulvene, 1.06 (6 mmol) in 5 mL of hexane was added dropwise at -78° C. The resulting yellow solution was stirred for 7 h at -78° C. Water, 25 mL, was added dropwise at -78° C. and the solution warmed to room temperature. The organic layer was separated and washed with aqueous NaHCO3, H2O and then dried over MgSO4. Removal of solvent gave 0.8 g (79% yield) of 1-cyclopentadienyl-1-phenylethane as a light yellow oil. [α]D =2.0 ° (CHCl3), 5.8% ee.

Aufarbeitung

  1. customThe solvent was removed under vacuum and 25 mL of hexane
  2. additionadded
  3. stirringThe resulting yellow solution was stirred for 7 h at -78° C
  4. temperaturethe solution warmed to room temperature
  5. customThe organic layer was separated
  6. washwashed with aqueous NaHCO3, H2O
  7. dry with materialdried over MgSO4
  8. customRemoval of solvent

Quellen und Nachweise

ORD-Eintrag
ord-23a2915ad1494c7286fe8a7ae6bea9be
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05349100

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