Hexane → 1-Cyclopentadienyl-1-(2,7-di-tert-butylfluorenyl)cyclohexane

HRID 1251530Notes

Reaction equation

HRID 1251530 reaction equation
[C:1]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCCCCC.C([Li])CCC.[CH:33]1([C:39]2[C:43](=C)[CH:42]=[CH:41][CH:40]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>O.C1COCC1>[CH:39]1([C:33]2([C:10]3[C:9]4[CH2:8][C:7]5[C:15](=[CH:16][CH:17]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=5)[C:14]=4[CH:13]=[CH:12][C:11]=3[C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:40]=[CH:41][CH:42]=[CH:43]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 40900822,7-Di-tert-butylfluoreneHCID 22327799CyclohexylfulveneHCID 178418339Butyllithium

Product 1

HCID 1317231041-Cyclopentadienyl-1-(2,7-di-tert-butylfluorenyl)cyclohexaneYield 67.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a THF (30 ml) solution including 5.0 g (18.6 mmol) of 2,7-di-tert-butylfluorene, a hexane solution (13.5 ml, 21.6 mmol) of n-butyllithium was added dropwise at −78° C. under nitrogen, followed by stirring at room temperature for 6 hours. Next, a THF (20 ml) solution including 3.42 g (23.4 mmol) of cyclohexylfulvene was added dropwise at 0° C. under a nitrogen atmosphere, followed by stirring at room temperature for 16 hours. The resultant reaction solution was decomposed with cold water, and then extracted with ether. The extract was dried over magnesium sulfate and then filtered, and the used solvent was removed from the filtrate under reduced pressure, thereby obtaining a solid. This solid was recrystallized from methanol to obtain 5.36 g of a colorless solid.

Workup

  1. additionwas added dropwise at 0° C. under a nitrogen atmosphere
  2. stirringby stirring at room temperature for 16 hours
  3. customThe resultant reaction solution
  4. extractionextracted with ether
  5. dry with materialThe extract was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe used solvent was removed from the filtrate under reduced pressure
  8. customobtaining a solid
  9. customThis solid was recrystallized from methanol

Sources & evidence

ORD record
ord-7c02aa446e3949f4a0b6f1a920c296a1
Source dataset
uspto-grants-2002_01
Patent number
US06342568B1

Reaction notes

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