Water → 2,2-Cyclopentadienyl(9-fluorenyl)-ethylbenzene

HRID 2687Notes

Reaction equation

HRID 2687 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.[Li].[CH3:15][C:16]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[C:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1.O>O1CCCC1>[CH:17]1([C:16]2[C:15]([CH:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)=[C:25]([CH2:24][CH3:23])[CH:26]=[CH:27][CH:22]=2)[CH2:18][CH2:19][CH:20]=[CH:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 5928226-Methyl-6-phenylfulveneHCID 69882698Lithium Fluorene

Product 1

HCID 227351332,2-Cyclopentadienyl(9-fluorenyl)-ethylbenzeneYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 67.8 mmol of lithiumfluorene in 50 cm3 of tetrahydrofuran is added to a solution of 11.4 g (67.8 mmol) of 6-methyl-6-phenyl-fulvene in 40 cm3 of tetrahydrofuran at room temperature. After the mixture had been stirred at room temperature for 2 hours, 60 cm3 of water were added. The substance which precipitated during this procedure was filtered off with suction, washed with diethyl ether and dried under an oil pump vacuum. 19.1 g (84.2%) of 2,2-cyclopentadienyl(9-fluorenyl)-ethylbenzene were obtained (correct elemental analyses; 1H-NMR spectra).

Workup

  1. customThe substance which precipitated during this procedure
  2. filtrationwas filtered off with suction
  3. washwashed with diethyl ether
  4. customdried under an oil pump vacuum

Sources & evidence

ORD record
ord-c0a3230366d04c2986114da6b17393e8
Source dataset
uspto-grants-1998_03
Patent number
US05731254

Reaction notes

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