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Fluorene → 5-(Cyclopentadienyl)-5-(fluoren-9-yl)-hex-1-ene

HRID 129094
Notes
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Reaction equation

HRID 129094 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>[C: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])[CH2:28][CH:27]=[CH:26][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

HCID 186223285-(Cyclopentadienyl)-5-(fluoren-9-yl)-hex-1-ene

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 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 solution was then added dropwise over a period of one half hour to the solution of the fluorenyl lithium salt. That 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-cyclopentdienyl-5-(9-fluorenyl)-1-hexene in a form of a white solid.

Workup

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

Sources & evidence

ORD record
ord-5a5bc54390b646aba6c9c35deebb964f
Source dataset
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05466766

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes