Hexane → 2-(3-Tert-butyl-5-methylcyclopentadienyl)-2-(2,7-di-tert-butylfluorenyl)propane

HRID 271012Notes

Reaction equation

HRID 271012 reaction equation
[C:1]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:22]CCCCC.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]>C1COCC1.O>[C:33]([C:37]1[CH:38]=[C:39]([CH3:22])[CH:40]([C:42]([C:10]2[C:9]3[CH2:8][C:7]4[C:15](=[CH:16][CH:17]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=4)[C:14]=3[CH:13]=[CH:12][C:11]=2[C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:44])[CH3:43])[CH:41]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 8058HexaneHCID 40900822,7-Di-tert-butylfluoreneHCID 146882832-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-dieneHCID 178418339Butyllithium

Product 1

HCID 1317251312-(3-Tert-butyl-5-methylcyclopentadienyl)-2-(2,7-di-tert-butylfluorenyl)propaneYield 71.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.45 g (8.80 mmol) of 2,7-di-tert-butylfluorene in 50 ml of THF, 5.67 ml (9.24 mmol) of a hexane solution of n-butyllithium was dropwise added in a nitrogen atmosphere at 0° C., followed by stirring at room temperature overnight. To the resulting solution, a solution of 2.85 g (17.6 mmol) of 3-tert-butyl-6,6-dimethylfulvene in 30 ml of THF was successively dropwise added in a nitrogen atmosphere at 0° C., followed by stirring at room temperature overnight to perform reaction. After the reaction, 30 ml of water was added. The organic phase was extracted with ether and dried over anhydrous magnesium sulfate. From the resulting solution, the solvent was distilled off to obtain a crude yellow solid. The solid was washed with methanol to obtain 2.77 g of a powdery white solid (yield: 71.5%.The analyzed values are given below.

Workup

  1. stirringby stirring at room temperature overnight
  2. customreaction
  3. additionwas added
  4. extractionThe organic phase was extracted with ether
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationFrom the resulting solution, the solvent was distilled off
  7. customto obtain a crude yellow solid
  8. washThe solid was washed with methanol

Sources & evidence

ORD record
ord-b4278bf42cd34cd9b393c95076c5b4f5
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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