Hexane → Methyl(p-tolyl)cyclopentadienyl(2,7-diphenyl-3,6-di-tert-butylfluorenyl)methane

HRID 630584Notes

Reaction equation

HRID 630584 reaction equation
C([Li])CCC.CCCCCC.C(C(C1C=CC(Cl)=CC=1)=[C:20]1[C:32]2[C:24]([CH:25]=[C:26]3[C:31]=2[CH:30]=[C:29]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:28]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:27]3)=[C:23](C2C=CC=C2)[C:22]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[C:21]1[C:54]([CH3:57])([CH3:56])[CH3:55])C1C=CC=CC=1.[CH3:65][C:66]([C:72]1[CH:77]=[CH:76][C:75]([CH3:78])=[CH:74][CH:73]=1)=[C:67]1[CH:71]=[CH:70][CH:69]=[CH:68]1>O1CCCC1>[CH3:65][C:66]([C:72]1[CH:73]=[CH:74][C:75]([CH3:78])=[CH:76][CH:77]=1)([CH:67]1[CH:68]=[CH:69][CH:70]=[CH:71]1)[C:23]1[C:24]2[CH2:25][C:26]3[C:31](=[CH:30][C:29]([C:33]([CH3:34])([CH3:36])[CH3:35])=[C:28]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:27]=3)[C:32]=2[CH:20]=[C:21]([C:54]([CH3:56])([CH3:55])[CH3:57])[C:22]=1[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 216764486-Methyl-6-(p-tolyl)fulveneHCID 131735408Benzyl(p-chlorophenyl)methylene(cyclopentadienyl)(2,7-diphenyl-3,6-di-tert-butylfluorene)HCID 178418339Butyllithium

Product 1

HCID 131735409Methyl(p-tolyl)cyclopentadienyl(2,7-diphenyl-3,6-di-tert-butylfluorenyl)methane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, a solution of n-butyllithium in hexane (6.3 ml, 10.2 mmol) was dropped into a solution of 2,7-diphenyl-3,6-di-tert-butylfluorene (4.0 g, 9.3 mmol) in dry tetrahydrofuran (50 ml) at −10° C., and then the product was stirred at room temperature for 20 hours. Then, 6-methyl-6-(p-tolyl)fulvene (1.9 g, 10.2 mmol) was dropped into this solution at −10° C., and the product was stirred at room temperature for 2 hours to induce a reaction. After the reaction was terminated, dilute aqueous hydrochloric acid was added thereto, the product was subjected to extraction with hexane, the organic layer was subsequently washed with water and then dehydrated with anhydrous magnesium sulfate, and then the solvent was distilled off to produce a light brown solid. The produced solid was recrystallized with methanol to obtain 5.1 g of an objective. The analytical values were as follows.

Workup

  1. stirringthe product was stirred at room temperature for 2 hours
  2. customa reaction
  3. customAfter the reaction was terminated
  4. additiondilute aqueous hydrochloric acid was added
  5. extractionthe product was subjected to extraction with hexane
  6. washthe organic layer was subsequently washed with water
  7. distillationthe solvent was distilled off
  8. customto produce a light brown solid
  9. customThe produced solid was recrystallized with methanol
  10. customto obtain 5.1 g of an objective

Sources & evidence

ORD record
ord-9ea0d5fa28814f3a8979288c0746ad30
Source dataset
uspto-grants-2016_04
Patent number
US09315602B2

Reaction notes

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