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

HRID 2226688Notes

Reaction equation

HRID 2226688 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.O>CCOCC.CCCCCC>[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

7

Reactant 4

HCID 962WaterHCID 5928226-Methyl-6-phenylfulveneHCID 178418339ButyllithiumHCID 178506840HCID 178506840, compound

Product 1

HCID 12445303[1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzeneYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

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. The solvent was removed under vacuum and 25 mL of hexane added. 6-Methyl-6-phenylfulvene, 1.06 (6 mmol) in 5 mL of hexane was added dropwise at -78° C. The resulting yellow solution was stirred for 7 h at -78° C. 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 0.8 g (79% yield) of 1-cyclopentadienyl-1-phenylethane as a light yellow oil. [α]D =2.0 ° (CHCl3), 5.8% ee.

Workup

  1. customThe solvent was removed under vacuum and 25 mL of hexane
  2. additionadded
  3. stirringThe resulting yellow solution was stirred for 7 h at -78° C
  4. temperaturethe solution warmed to room temperature
  5. customThe organic layer was separated
  6. washwashed with aqueous NaHCO3, H2O
  7. dry with materialdried over MgSO4
  8. customRemoval of solvent

Sources & evidence

ORD record
ord-23a2915ad1494c7286fe8a7ae6bea9be
Source dataset
uspto-grants-1994_09
Patent number
US05349100

Reaction notes

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