Hexane → 2-(3-Tert-butylcyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propane

HRID 495727Notes

Reaction equation

HRID 495727 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.[C:33]([C:37]1[CH:38]=[CH:39][C:40](=[C:42]([CH3:44])[CH3:43])[CH:41]=1)([CH3:36])([CH3:35])[CH3:34]>CCOCC.O>[C:33]([C:37]1[CH:38]=[CH:39][CH:40]([C:42]([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])[CH3:43])[CH:41]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 146882832-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-dieneHCID 178418339Butyllithium

Product 1

HCID 1317251212-(3-Tert-butylcyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propaneYield 43.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1.98 g (7.1 mmol) of 3,6-di-tert-butylfluorene in 40 ml of ether, 4.6 ml (7.5 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 1.56 g (9.6 mmol) of 3-tert-butyl-6,6-dimethylfulvene in 20 ml of ether was further dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 60 ml of water was added. The separated organic phase was dried over magnesium sulfate and then filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid was purified by column chromatography (silica gel, developing solvent: hexane) to obtain 1.35 g of a light yellow solid (yield: 43%). The analyzed values are given below.

Workup

  1. stirringby stirring at room temperature for one night
  2. dry with materialThe separated organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customFrom the filtrate, the solvent was removed under reduced pressure
  5. customto obtain a solid
  6. customThe solid was purified by column chromatography (silica gel, developing solvent: hexane)

Sources & evidence

ORD record
ord-75f54e6b203040c89f315ac63b78dd08
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

Loading…