Fluorene → 5-Cyclopentadienyl-5-(9-fluorenyl)-1-hexene

HRID 1440190Notes

Reaction equation

HRID 1440190 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH:19]([C:23]([CH3:29])=[C:24]1[CH:28]=[CH:27][CH:26]=[CH:25]1)=[CH:20][CH2:21][CH3:22].C1([Li])C2CC3C(=CC=CC=3)C=2C=CC=1>C1COCC1.CCCCCC.O>[CH:24]1([C:23]([CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)([CH3:29])[CH2:19][CH2:20][CH:21]=[CH2:22])[CH:28]=[CH:27][CH:26]=[CH:25]1

Participants

8

Reactant 4

HCID 6853FluoreneHCID 540533226-Butenyl-6-methylfulveneHCID 178418339ButyllithiumHCID 178506660HCID 178506660, compound

Product 1

HCID 158619165-Cyclopentadienyl-5-(9-fluorenyl)-1-hexene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution was prepared by dissolving 10 g of fluorene in 100 mL of THF and then this was slowly reacted with 37.6 mL of a 1.6 molar solution of n-butyllithium in hexane. This dark red solution was stirred overnight at room temperature. Then a solution was prepared by combining 8.8 g of 6-(butenyl)-6-methylfulvene with 50 mL of THF. This later solution was then added dropwise over a period of one half hour to the solution of the fluorenyl lithium salt. The resulting reaction mixture was stirred overnight at room temperature and then 100 mL of water was added. The organic phase was dried overnight over sodium sulfate and the solvent was evaporated in a vacuum. The yellow residue was dissolved in pentane and filtered using silica gel. The solvent was concentrated by means of evaporation. Crystallization took place at about -18° C. to give 5-(cyclopentadienyl)-5-(9-fluorenyl)-1-hexene in the form of a white solid. This compound is also sometimes referred to as 1-(9-fluorenyl)-1-(cyclopentadienyl)-1-(but-3-enyl)-1-(methyl) methane.

Workup

  1. customA solution was prepared
  2. customThen a solution was prepared
  3. customThe resulting reaction mixture
  4. stirringwas stirred overnight at room temperature
  5. dry with materialThe organic phase was dried overnight over sodium sulfate
  6. customthe solvent was evaporated in a vacuum
  7. dissolutionThe yellow residue was dissolved in pentane
  8. filtrationfiltered
  9. concentrationThe solvent was concentrated by means of evaporation
  10. customCrystallization
  11. customat about -18° C.

Sources & evidence

ORD record
ord-df0a9d01ed404a32b2c0c1b9de19d3d6
Source dataset
uspto-grants-1996_03
Patent number
US05498581

Reaction notes

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