Hexane → 1-(Cyclopentadienyl)-1(3,6-di-tert-butylfluorenyl)diphenylmethane

HRID 495753Notes

Reaction equation

HRID 495753 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]1([C:39]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[C:40]2[CH:44]=[CH:43][CH:42]=[CH:41]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1.O>[CH:40]1([C:39]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[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)[CH:41]=[CH:42][CH:43]=[CH:44]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 1012366,6'-DiphenylfulveneHCID 111404373,6-DI-Tert-butylfluoreneHCID 178418339Butyllithium

Product 1

HCID 1317251321-(Cyclopentadienyl)-1(3,6-di-tert-butylfluorenyl)diphenylmethane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.5 g (9.0 mmol) of 3,6-di-tert-butylfluorene in 40 ml of THF, 6.1 ml (9.8 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 4 hours. The resulting solution was ice cooled again, and thereto was dropwise added a solution of 2.5 g (10.8 mmol) of 6,6-diphenylfulvene in 30 ml of THF in a nitrogen atmosphere, followed by stirring at room temperature for 5 hours. Then, 50 ml of water was added. The organic phase extracted with diethyl ether and separated 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 recrystallized from methanol to obtain 3.4 g of a slightly yellow solid. The analyzed values are given below. 1H-NMR (270 MHz, in CDCl3, Based on TMS): δ7.47 (s, 2H), 7.28 (br, 4H), 7.07−7.01 (br, 10H), 6.51−6.18 (m, 3H), 5.46+5.41 (s+s, 1H), 2.94+2.86 (s+s, 2H), 1.30 (s, 18H)

Workup

  1. temperaturecooled again
  2. stirringby stirring at room temperature for 5 hours
  3. extractionThe organic phase extracted with diethyl ether
  4. customseparated
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. customFrom the filtrate, the solvent was removed under reduced pressure
  8. customto obtain a solid
  9. customThe solid was recrystallized from methanol
  10. customto obtain 3.4 g of a slightly yellow solid

Sources & evidence

ORD record
ord-2c609c9d0900486a9c3bb0222be6173b
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

Loading…