Hexane → 2-(3-(1,1-Dimethylpropyl)cyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propane

HRID 270997Notes

Reaction equation

HRID 270997 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]([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]([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)([CH3:44])[CH3:45])[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 1317251262-(3-(1,1-Dimethylpropyl)cyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propaneYield 59%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.14 g (7.7 mmol) of 3,6-di-tert-butylfluorene in 40 ml of THF, 5.0 ml (8.1 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 1.81 g (10.3 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 3 days. 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 2.06 g (4.53 mmbl) of a white solid (yield: 59%). The analyzed values are given below.

Workup

  1. stirringby stirring at room temperature for 3 days
  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-7eace6301274482588a0215787328afc
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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