Water → 1,1-Cyclopentadienyl(9-fluorenyl)dipenylmethane

HRID 2253854Notes

Reaction equation

HRID 2253854 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH:6]1[C:18]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.[C:19]1([C:25]2[CH:29]=[CH:28][C:27](=[CH2:30])[C:26]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)C=CC=CC=1.O.[CH3:38]CCCCC>O1CCCC1.[Cl-].[Cl-].C1(C(=[Zr+2](C2C3C=CC=CC=3C3C2=CC=CC=3)C2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1>[C:4]1([C:26]([CH:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[C:18]2=[CH:6][CH:7]=[CH:8][CH:9]=3)([C:25]2[CH:19]=[CH:30][CH:27]=[CH:28][CH:29]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:38][CH2:1][CH2:2][CH:3]=1

Participants

8

Reactant 5

HCID 962WaterHCID 6853FluoreneHCID 8058HexaneHCID 22238549Diphenyl FulveneHCID 178418339Butyllithium

Product 1

HCID 227351321,1-Cyclopentadienyl(9-fluorenyl)dipenylmethaneYield 42%

Reagents, catalysts & solvents 2

HCID 178420589HCID 178420589, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Diphenylmethylene(9-fluorenyl)(cyclopentadienyl)zirconium dichloride ##STR11## 12.3 cm3 (30.7 mmol) of a 2.5 molar solution of n-butyllithium in hexane were slowly added to a solution of 5.10 g (30.7 mmol) of fluorene in 60 cm3 of tetrahydrofuran at room temperature. After 40 minutes, 7.07 g (30.7 mmol) of diphenylfulvene were added to the orange solution and the mixture was stirred overnight. 60 cm3 of water were added to the dark red solution, whereupon the solution became yellow in color, and the solution was extracted with ether. The ether phase was dried over MgSO4 and concentrated and the concentrate was left to crystallize at -35° C. 5.1 g (42%) of 1,1-cyclopentadienyl-(9-fluorenyl)diphenylmethane were obtained as a beige powder.

Workup

  1. extractionthe solution was extracted with ether
  2. dry with materialThe ether phase was dried over MgSO4
  3. concentrationconcentrated
  4. waitthe concentrate was left
  5. customto crystallize at -35° C

Sources & evidence

ORD record
ord-162d04fd3c194e18bd2a055ac47bf836
Source dataset
uspto-grants-1993_08
Patent number
US05232993

Reaction notes

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