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

HRID 2226684Notes

Reaction equation

HRID 2226684 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6dc8c1949d4e427b9d0222f4d991cc19
Source dataset
uspto-grants-1994_09
Patent number
US05349100

Reaction notes

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