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

HRID 1493072

Reaction equation

HRID 1493072 reaction equation
[CH3:1]CCCCC.[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[CH:12]1[C:24]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1.[C:25]1([C:31]2[CH:35]=[CH:34][C:33](=[CH2:36])[C:32]=2[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)C=CC=CC=1>O1CCCC1.O>[C:10]1([C:32]([CH:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[C:24]2=[CH:12][CH:13]=[CH:14][CH:15]=3)([C:31]2[CH:25]=[CH:36][CH:33]=[CH:34][CH:35]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:1][CH2:7][CH2:8][CH:9]=1

Participants

7

Reactant 4

HCID 6853FluoreneHCID 8058HexaneHCID 22238549Diphenyl FulveneHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

12.3 cm3 (30.7 mmol) of a 2.5 molar hexane solution of n-butyllithium 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 residue 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 residue was left
  5. customto crystallize at -35° C

Sources & evidence

ORD record
ord-d58657b61e5444edab7720b812f48d43
Source dataset
uspto-grants-1994_12
Patent number
US05376725

Linked notes

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