Fluorene → 2-(3-Tert-butyl-5-methylcyclopentadienyl)-2-fluorenylpropane

HRID 495725Notes

Reaction equation

HRID 495725 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CCCCCC.C([Li])CCC.[C:25]([C:29]1[CH:30]=[C:31]([CH3:37])[C:32](=[C:34]([CH3:36])[CH3:35])[CH:33]=1)([CH3:28])([CH3:27])[CH3:26]>C1COCC1.O>[C:25]([C:29]1[CH:30]=[C:31]([CH3:37])[CH:32]([C:34]([C:1]2[C:13]3[CH2:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[CH:4]=[CH:3][CH:2]=2)([CH3:36])[CH3:35])[CH:33]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 6853FluoreneHCID 8058HexaneHCID 27627611,6,6-Trimethyl-3-tert-butyl-fulveneHCID 178418339Butyllithium

Product 1

HCID 1317251202-(3-Tert-butyl-5-methylcyclopentadienyl)-2-fluorenylpropaneYield 18.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 10.1 g (60.8 mmol) of fluorene in 300 ml of THF, 40 ml (61.6 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 5 hours (dark brown solution). The solution was ice cooled again, and a solution of 11.7 g (66.5 mmol) of 3-tert-butyl-1,6,6-trimethylfulvene in 300 ml of THF was dropwise added in a nitrogen atmosphere. After stirring at room temperature for 14 hours, the resulting brown solution was ice cooled, and 200 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 an orangy brown oil. The oil was purified by silica gel column chromatography (developing solvent: hexane) to obtain 3.8 g of a yellow oil. The analyzed values are given below.

Workup

  1. temperaturecooled again
  2. stirringAfter stirring at room temperature for 14 hours
  3. temperaturecooled
  4. extractionThe organic phase extracted with diethyl ether
  5. customseparated
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. customFrom the filtrate, the solvent was removed under reduced pressure
  9. customto obtain an orangy brown oil
  10. customThe oil was purified by silica gel column chromatography (developing solvent: hexane)

Sources & evidence

ORD record
ord-86b8ecabcf9c4c85bb475ac06710478b
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

Loading…