1,3-Dimethyl-2-imidazolidinone → Di(p-chlorophenyl)cyclopentadienyl(octamethyloctahydrodibenzofluorenyl)methane

HRID 423126Notes

Reaction equation

HRID 423126 reaction equation
[CH3:1][C:2]1([CH3:29])[CH:7]2[CH:8]3[CH2:22][CH2:21][CH:20]=[CH:19][C:9]3=[C:10]3[C:18]([CH2:17][C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]3=4)=[C:6]2[C:5](C)([CH3:23])[C:4]([CH3:26])([CH3:25])[C:3]1([CH3:28])[CH3:27].[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=2)=[C:38]2[CH:42]=[CH:41][CH:40]=[CH:39]2)=[CH:33][CH:32]=1.[CH3:50]CCCCC.C([Li])CCC.CN1CCN(C)C1=O>O1CCCC1>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([C:43]2[CH:44]=[CH:45][C:46]([Cl:49])=[CH:47][CH:48]=2)([CH:38]2[CH:39]=[CH:40][CH:41]=[CH:42]2)[C:7]2([CH3:50])[C:6]3[C:5]([CH3:23])([CH:12]4[CH2:13][CH2:14][CH:15]=[CH:16][C:11]4=[C:10]4[C:18]=3[CH2:17][C:19]3[CH:20]=[CH:21][CH:22]=[CH:8][C:9]4=3)[C:4]([CH3:26])([CH3:25])[C:3]([CH3:28])([CH3:27])[C:2]2([CH3:1])[CH3:29])=[CH:35][CH:36]=1

Participants

7

Reactant 5

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 8058HexaneHCID 118334636,6-Di(p-chlorophenyl)fulvene2×HCID 86606716OctamethyloctahydrodibenzofluoreneHCID 178418339Butyllithium

Product 1

HCID 131729404Di(p-chlorophenyl)cyclopentadienyl(octamethyloctahydrodibenzofluorenyl)methaneYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A reaction vessel equipped with a dropping funnel was charged with 40 ml of dehydrated tetrahydrofuran and 2.35 g (6.08 mmol) of octamethyloctahydrodibenzofluorene synthesized by a method described in (i) of Synthetic Example 1 under nitrogen atmosphere, and 4.62 ml (7.30 mmol) of a hexane solution of n-butyllithium of 1.58 mol/L was added dropwise and stirred while cooling the above solution at 0° C. 1,3-Dimethyl-2-imidazolidinone 0.86 ml (7.90 mmol) was added to the above solution and stirred for 30 minutes. Then, a solution prepared by dissolving 2.00 g (6.68 mmol) of 6,6-di(p-chlorophenyl)fulvene in 30 ml of dehydrated tetrahydrofuran was [put] placed in the dropping funnel and added dropwise while cooling at −78° C., and the solution was stirred for one day while slowly allowing it to return to room temperature. This reaction solution was extracted with diethyl ether, and the separated organic layer was washed with 1N hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution and a saturated salt solution and dried over anhydrous magnesium sulfate. Then, magnesium sulfate was removed by filtration, and the solvent contained in the filtrate was removed by distillation under reduced pressure by means of a rotary evaporator. The residue was purified through a silica gel column and then recrystallized from toluene to obtain a targeted product (amount obtained: 0.714 g, yield: 17%). The targeted product was identified by means of 1H-NMR and FD-MS spectra.

Workup

  1. customA reaction vessel equipped with a dropping funnel
  2. customsynthesized by a method
  3. stirringstirred for 30 minutes
  4. customThen, a solution prepared
  5. additionadded dropwise
  6. temperaturewhile cooling at −78° C.
  7. stirringthe solution was stirred for one day
  8. customto return to room temperature
  9. extractionThis reaction solution was extracted with diethyl ether
  10. washthe separated organic layer was washed with 1N hydrochloric acid
  11. dry with materiala saturated sodium hydrogen carbonate aqueous solution and a saturated salt solution and dried over anhydrous magnesium sulfate
  12. customThen, magnesium sulfate was removed by filtration
  13. customwas removed by distillation under reduced pressure by means of a rotary evaporator
  14. customThe residue was purified through a silica gel column
  15. customrecrystallized from toluene
  16. customto obtain
  17. customa targeted product (amount obtained: 0.714 g, yield: 17%)

Sources & evidence

ORD record
ord-fe3d1fa3598443b6ae2f3d930b118f05
Source dataset
uspto-grants-2012_01
Patent number
US08101684B2

Reaction notes

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