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

HRID 1050668
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HRID 1050668 반응식
[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].[CH2:30]([Li])CCC.CN1CCN(C)C1=O.[Cl:43][C:44]1[CH:49]=[CH:48][C:47]([C:50]([C:56]2[CH:61]=[CH:60][C:59]([Cl:62])=[CH:58][CH:57]=2)=[C:51]2[CH:55]=[CH:54][CH:53]=[CH:52]2)=[CH:46][CH:45]=1>O1CCCC1.CCCCCC>[Cl:43][C:44]1[CH:45]=[CH:46][C:47]([C:50]([C:56]2[CH:57]=[CH:58][C:59]([Cl:62])=[CH:60][CH:61]=2)([CH:51]2[CH:52]=[CH:53][CH:54]=[CH:55]2)[C:7]2([CH3:30])[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:48][CH:49]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 118334636,6-Di(p-chlorophenyl)fulveneHCID 86606716OctamethyloctahydrodibenzofluoreneHCID 178418339Butyllithium

생성물 1

HCID 131729404Di(p-chlorophenyl)cyclopentadienyl(octamethyloctahydrodibenzofluorenyl)methane

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
2회
HCID 8058Hexane용매

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온도
0 °C

실험 절차

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 in Synthesis Example 2-1 under a nitrogen atmosphere. Then, 4.62 ml (7.30 mmol) of a 1.58 mol/L hexane solution of n-butyllithium was slowly added dropwise and while cooling this solution to 0° C., and the mixture was stirred. Then, 0.86 ml (7.90 mmol) of 1,3-dimethyl-2-imidazolidinone was added to the solution and the mixture was stirred for 30 minutes. Subsequently, the dropping funnel was charged with a solution prepared by dissolving 2.00 g (6.68 mmol) of 6,6-di{p-chlorophenyl}fulvene in 30 ml of dehydrated tetrahydrofuran. The solution was slowly added dropwise while cooling the solution to −78° C. The mixture was stirred for one day while returning the temperature thereof slowly to room temperature. This reaction solution was subjected to extraction with diethyl ether. The organic layer was washed with 1 N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated brine. The organic phase collected by separation was dried over anhydrous magnesium sulfate and magnesium sulfate was separated by filtration. The filtrate was subjected to distillation under reduced pressure using a rotary evaporator to remove the solvent. The residue was purified by using a silica gel column and recrystallized from toluene to obtain a target product (yield 0.714 g (17%)). The target product was identified by 1H-NMR and FD-MS spectroscopy.

후처리

  1. customA reaction vessel equipped with a dropping funnel
  2. customsynthesized in Synthesis Example 2-1 under a nitrogen atmosphere
  3. stirringthe mixture was stirred for 30 minutes
  4. additionSubsequently, the dropping funnel was charged with a solution
  5. customprepared
  6. additionThe solution was slowly added dropwise
  7. temperaturewhile cooling the solution to −78° C
  8. stirringThe mixture was stirred for one day
  9. customslowly to room temperature
  10. extractionThis reaction solution was subjected to extraction with diethyl ether
  11. washThe organic layer was washed with 1 N hydrochloric acid
  12. customThe organic phase collected by separation
  13. dry with materialwas dried over anhydrous magnesium sulfate and magnesium sulfate
  14. customwas separated by filtration
  15. distillationThe filtrate was subjected to distillation under reduced pressure
  16. customa rotary evaporator
  17. customto remove the solvent
  18. customThe residue was purified
  19. customrecrystallized from toluene
  20. customto obtain a target product (yield 0.714 g (17%))

출처 및 근거

ORD 기록
ord-7dc229ecb7294af3b5374b3f2e5931d3
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09382356B2

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