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

HRID 271005Notes

Reaction equation

HRID 271005 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:40]1[CH:41]=[CH:42][C:43](=[C:45]([CH3:47])[CH3:46])[CH:44]=1)([CH3:39])[CH2:35][CH:36]([CH3:38])[CH3:37]>C1COCC1.CCOCC.O>[CH3:39][C:34]([C:40]1[CH:41]=[CH:42][CH:43]([C:45]([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)([CH3:47])[CH3:46])[CH:44]=1)([CH3:33])[CH2:35][CH:36]([CH3:38])[CH3:37]

Participants

8

Reactant 4

HCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 22327777HCID 22327777, compoundHCID 178418339Butyllithium

Product 1

HCID 1317251282-(3-(1,1,3-Trimethylbutyl)cyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propaneYield 74.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.16 g (7.8 mmol) of 3,6-di-tert-butylfluorene in 35 ml of THF, 5.0 ml (8.2 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 2.16 g (10.6 mmol) of 3-(1,1,3-trimethylbutyl)-6,6-dimethylfulvene in 10 ml of THF was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for 5 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 2.80 g (5.80 mmol) of a white solid (yield: 74%). The analyzed values are given below.

Workup

  1. stirringby stirring at room temperature for 5 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-1be8a0620c0b4969a2aaf1fa5939f047
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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