6-Methyl-6-phenylfulvene → [1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzene

HRID 2226685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226685
[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>CCOCC>[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

5

Edukt 3

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

Produkt 1

HCID 12445303[1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzeneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of 0.77 g 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 hexances, 13 mmol) at 0° C. This solution was stirred for 30 min at room temperature. 6-Methyl-6-phenylfulvene, 1.0 g, (6 mmol) in 5 mL of ether was added dropwise at -78° C. and the color of the reaction mixture turned green. The resulting solution was stirred for 7 h 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 1.0 g (99% yield) of 1-cyclopentadienyl-1-phenyl-ethane as a light yellow oil. [α]D =6.0° (CHCl3), 17.4% ee.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-69bfc291c1b24ea186012bd2aa8cc485
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05349100

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