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

HRID 2226687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226687
[Li][C@H:2]1[CH2:6][CH:5]([C:7](O)=O)N([Li])[C:3]1=O.[Li][CH2:13][CH2:14][CH2:15][CH3:16]>CCOCC>[CH:2]1([CH:15]([C:14]2[CH:13]=[CH:5][CH:6]=[CH:2][CH:3]=2)[CH3:16])[CH:6]=[CH:5][CH:7]=[CH:3]1

Komponenten

4

Edukt 2

HCID 178418339ButyllithiumHCID 178506840HCID 178506840, Verbindung

Produkt 1

HCID 12445303[1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzeneAusbeute 176,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

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 (1.6 m 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 ether added. 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 color of the reaction mixture turned yellow. 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 0.9 g (89% 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 ether
  2. additionadded
  3. addition6-Methyl-6-phenylfulvene, 1.0 g, (6 mmol) in 5 mL of ether was added dropwise at -78° C.
  4. stirringThe resulting solution was stirred for 7 h at -78° C.
  5. additionWater, 25 mL, was added dropwise at -78° C.
  6. temperaturethe solution warmed to room temperature
  7. customThe organic layer was separated
  8. washwashed with aqueous NaHCO3, H2O
  9. dry with materialdried over MgSO4
  10. customRemoval of solvent

Quellen und Nachweise

ORD-Eintrag
ord-191b60158e024e0b8160cc188bfe6640
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05349100

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