Benzophenone → 3,6,6-Triphenylfulvene

HRID 271016Notes

Reaction equation

HRID 271016 reaction equation
[C:1]1([C:7]2[CH2:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCCCC.C([Li])CCC.[C:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.C1COCC1.O>[C:1]1([C:7]2[CH:11]=[CH:10][C:9](=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 3102BenzophenoneHCID 8058HexaneHCID 244167PhenylcyclopentadieneHCID 178418339Butyllithium

Product 1

HCID 223278143,6,6-Triphenylfulvene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.5 g (17.6 mmol) of phenylcyclopentadiene in 30 ml of toluene was ice cooled, and thereto was dropwise added 13.0 ml (21.1 mmol) of a hexane solution of n-butyllithium. The resulting white slurry was stirred at room temperature for one night. From the slurry, the solvent was filtered off to give a THF solution (brown solution). To the solution, a solution of 3.2 g (17.6 mmol) of benzophenone in 10 ml of THF was added, followed by stirring at room temperature for one night. After addition of water, the mixture was subjected to extraction with diethyl ether and dried over magnesium sulfate. Then, the ether was distilled off to obtain a red viscous liquid. The liquid was purified by a silica gel column to obtain a red solid.

Workup

  1. temperaturecooled
  2. filtrationFrom the slurry, the solvent was filtered off
  3. customto give a THF solution (brown solution)
  4. stirringby stirring at room temperature for one night
  5. extractionthe mixture was subjected to extraction with diethyl ether
  6. dry with materialdried over magnesium sulfate
  7. distillationThen, the ether was distilled off
  8. customto obtain a red viscous liquid
  9. customThe liquid was purified by a silica gel column
  10. customto obtain a red solid

Sources & evidence

ORD record
ord-9538ae9ec82c41fbab9c7eae5f1a1ab0
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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