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

HRID 495730Notes

Reaction equation

HRID 495730 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]1([C:40]2[CH:41]=[CH:42][C:43](=[C:45]([CH3:47])[CH3:46])[CH:44]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C1COCC1.CCOCC.O>[CH3:33][C:34]1([C:40]2[CH:41]=[CH:42][CH:43]([C:45]([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)([CH3:47])[CH3:46])[CH:44]=2)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1

Participants

8

Reactant 4

HCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 146882823-(1-Methyl-1-cyclohexyl)-6,6-dimethylfulveneHCID 178418339Butyllithium

Product 1

HCID 1317251222-(3-(1-Methyl-1-cyclohexyl)cyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propaneYield 43%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.64 g (9.5 mmol) of 3,6-di-tert-butylfluorene in 45 ml of THF, 6.4 ml (10.4 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 (9.9 mmol) of 3-(1-methyl-1-cyclohexyl)-6,6-dimethylfulvene in 30 ml of THF was further 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 1.96 g (4.08 mmol) of a white solid (yield: 43%). 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-77322e9a27294808b99a81db004062d9
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

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