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

HRID 2226689Notes

Reaction equation

HRID 2226689 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 EtherSolvent

Procedure

To a solution of 0.77 mL 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 hexanes, 13 mmol) at 0° C. This solution was stirred for 30 min at room temperature. 6-Methyl-6phenylfulvene, 1.0 g, (6 mmol) was added dropwise at 0° 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-phenylethane as a light yellow oil. [α]D =0.0° (CHCl3).

Workup

  1. temperaturethe solution warmed to room temperature
  2. customThe organic layer was separated
  3. washwashed with aqueous NaHCO3, H2O
  4. dry with materialdried over MgSO4
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-fce0989bdad141619ef2d8d90dc88def
Source dataset
uspto-grants-1994_09
Patent number
US05349100

Reaction notes

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