Hexane → 2-(Cyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propane

HRID 495747Notes

Reaction equation

HRID 495747 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:11]=3)([CH3:4])([CH3:3])[CH3:2].CCCCCC.C([Li])CCC.[CH3:33][C:34]([CH3:40])=[C:35]1[CH:39]=[CH:38][CH:37]=[CH:36]1>C1COCC1.O>[CH:35]1([C:34]([C:11]2[C:10]3[CH2:9][C:8]4[C:16](=[CH:17][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=4)[C:15]=3[CH:14]=[C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=2)([CH3:40])[CH3:33])[CH:39]=[CH:38][CH:37]=[CH:36]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 1374671,3-Cyclopentadiene, 5-(1-methylethylidene)-HCID 111404373,6-DI-Tert-butylfluoreneHCID 178418339Butyllithium

Product 1

HCID 1317251292-(Cyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 3.0 g(10.8 mmol) of 3,6-di-tert-butylfluorene in 40 ml of THF, 7.0 ml (11.3 mmol) of a hexane solution of n-butyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for 6 hours. From the reaction mixture, the solvent was removed under reduced pressure, and the residue was washed with pentane and dried to obtain a white solid. To a solution of the solid in 30 ml of THF, a solution of 1.4 g (13.2 mmol) of 6,6-dimethylfulvene in 30 ml of THF was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring for 5 hours. Then, 30 ml of water was added. The organic phase extracted with diethyl ether and separated was dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid was recrystallized from methanol to obtain 2.9 g of a slightly yellow solid. The analyzed values are given below.

Workup

  1. customFrom the reaction mixture, the solvent was removed under reduced pressure
  2. washthe residue was washed with pentane
  3. customdried
  4. customto obtain a white solid
  5. stirringby stirring for 5 hours
  6. extractionThe organic phase extracted with diethyl ether
  7. customseparated
  8. dry with materialwas dried over magnesium sulfate
  9. filtrationfiltered
  10. customFrom the filtrate, the solvent was removed under reduced pressure
  11. customto obtain a solid
  12. customThe solid was recrystallized from methanol
  13. customto obtain 2.9 g of a slightly yellow solid

Sources & evidence

ORD record
ord-976b8f1f1d654706831fb864bb6c1355
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

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