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

HRID 2226684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226684
N1CCC[C@H]1C(O)=O.[Li]CCCC.[CH3:14][C:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.O>CCOCC>[CH:16]1([CH:15]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH3:14])[CH:20]=[CH:19][CH:18]=[CH:17]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 145742L-ProlineHCID 5928226-Methyl-6-phenylfulveneHCID 178418339Butyllithium

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 1.4 g. of l-proline (12 mmol) in 40 mL of ether was added 15 mL of n-BuLi (1.6M solution in hexanes, 24 mmol) at 0° C. This solution was stirred overnight at room temperature and then cooled to -78° C. 6-Methyl-6-phenylfulvene, 2.0 g, (12 mmol) in 5 mL of ether was added dropwise at -78° C. The resulting solution was stirred 6 h at -78° C. Water, 20 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 the solvent gave 2.0 g (99% yield) of 1-cyclopentadienyl-1-phenylethane as a light yellow oil. D =3.0° (CHCl3), 8.7% ee.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6dc8c1949d4e427b9d0222f4d991cc19
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05349100

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