Hexane → 1-(3-(1,1-Dimethylpropyl)cyclopentadienyl)-1-(3,6-di-tert-butylfluorenyl)cyclohexane

HRID 495765Notes

Reaction equation

HRID 495765 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].[CH3:22][CH2:23][CH2:24]CCC.C([Li])CCC.[CH3:33][C:34]([C:38]1[CH:39]=[CH:40][C:41](=[C:43]([CH3:45])[CH3:44])[CH:42]=1)([CH3:37])[CH2:35][CH3:36]>C1COCC1.CCOCC.O>[CH3:37][C:34]([C:38]1[CH:39]=[CH:40][CH:41]([C:43]2([C:11]3[C:10]4[CH2:9][C:8]5[C:16](=[CH:17][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=5)[C:15]=4[CH:14]=[C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=3)[CH2:44][CH2:24][CH2:23][CH2:22][CH2:45]2)[CH:42]=1)([CH3:33])[CH2:35][CH3:36]

Participants

8

Reactant 4

HCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 178181473-(1,1-Dimethylpropyl)-6,6-dimethylfulveneHCID 178418339Butyllithium

Product 1

HCID 1317251411-(3-(1,1-Dimethylpropyl)cyclopentadienyl)-1-(3,6-di-tert-butylfluorenyl)cyclohexaneYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.38 g (8.5 mmol) of 3,6-di-tert-butylfluorene in 40 ml of THF, 5.7 ml (9.2 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 one night. To the resulting red solution, a solution of 2.00 g (9.2 mmol) of 3-(1,1-dimethylpropyl)-6,6-dimethylfulvene in 30 ml of THF was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 100 ml of ether, 50 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was isolated and purified by column chromatography (silica gel, developing solvent: hexane) to obtain 1.88 g (3.80 mmol) of a white solid (yield: 45%). The analyzed values are given below.

Workup

  1. stirringby stirring at room temperature for one night
  2. additionwas added
  3. washThe separated organic phase was washed with water
  4. dry with materiala saturated saline solution, then dried over magnesium sulfate
  5. filtrationfiltered
  6. customFrom the filtrate, the solvent was removed under reduced pressure
  7. customto obtain a liquid
  8. customThe liquid was isolated
  9. custompurified by column chromatography (silica gel, developing solvent: hexane)

Sources & evidence

ORD record
ord-7b5848895bd14bab8c3306e778297263
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

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