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

HRID 2226685Notes

Reaction equation

HRID 2226685 reaction equation
[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

Participants

5

Reactant 3

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

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 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.

Workup

  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

Sources & evidence

ORD record
ord-69bfc291c1b24ea186012bd2aa8cc485
Source dataset
uspto-grants-1994_09
Patent number
US05349100

Reaction notes

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