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

HRID 2226687Notes

Reaction equation

HRID 2226687 reaction equation
[Li][C@H:2]1[CH2:6][CH:5]([C:7](O)=O)N([Li])[C:3]1=O.[Li][CH2:13][CH2:14][CH2:15][CH3:16]>CCOCC>[CH:2]1([CH:15]([C:14]2[CH:13]=[CH:5][CH:6]=[CH:2][CH:3]=2)[CH3:16])[CH:6]=[CH:5][CH:7]=[CH:3]1

Participants

4

Reactant 2

HCID 178418339ButyllithiumHCID 178506840HCID 178506840, compound

Product 1

HCID 12445303[1-(Cyclopenta-2,4-dien-1-yl)ethyl]benzeneYield 176.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 (1.6 m 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 ether added. 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 color of the reaction mixture turned yellow. 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 0.9 g (89% 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 ether
  2. additionadded
  3. addition6-Methyl-6-phenylfulvene, 1.0 g, (6 mmol) in 5 mL of ether was added dropwise at -78° C.
  4. stirringThe resulting solution was stirred for 7 h at -78° C.
  5. additionWater, 25 mL, was added dropwise at -78° C.
  6. temperaturethe solution warmed to room temperature
  7. customThe organic layer was separated
  8. washwashed with aqueous NaHCO3, H2O
  9. dry with materialdried over MgSO4
  10. customRemoval of solvent

Sources & evidence

ORD record
ord-191b60158e024e0b8160cc188bfe6640
Source dataset
uspto-grants-1994_09
Patent number
US05349100

Reaction notes

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