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Ethylcyclopentadiene → HCID 178438266, 화합물

HRID 735298
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HRID 735298 반응식
[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Ta+5].C([Mg]Br)(C)C.C(C1([Li])C=CC=C1)C.C(C1CC=CC=1)C.C([Li])CCC.[CH2:32]([C:34]1([Ta:39]([C:42]2([CH2:47][CH3:48])[CH:46]=[CH:45][CH:44]=[CH:43]2)(Cl)Cl)[CH:38]=[CH:37][CH:36]=[CH:35]1)[CH3:33].[H-].COCCO[Al+]OCCOC.[Na+].[H-]>CCOCC.C1COCC1.O.C1(C)C=CC=CC=1>[CH2:47]([C:42]1([TaH3:39][C:34]2([CH2:32][CH3:33])[CH:38]=[CH:37][CH:36]=[CH:35]2)[CH:46]=[CH:45][CH:44]=[CH:43]1)[CH3:48]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

12

반응물 7

HCID 528166EthylcyclopentadieneHCID 10269745Tantalum chlorideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 178418339ButyllithiumHCID 178418365HCID 178418365, 화합물HCID 178438265HCID 178438265, 화합물HCID 178506694HCID 178506694, 화합물

생성물 1

HCID 178438266HCID 178438266, 화합물수율 10.1%

시약·촉매·용매 4

HCID 962Water용매HCID 1140Toluene용매2회HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
-70 °C

실험 절차

75.0 g (209 mmol) of tantalum pentachloride was suspended in 1,200 ml of ether, and 335 ml (228 mmol) of isopropyl magnesium bromide (0.68M THF solution) was added thereto. A solution of 41.9 g (419 mmol) of ethylcylopentadienyl lithium prepared from ethylcylopentadiene and butyl lithium in THF (240 ml) was added, followed by refluxing for 1 hour. The solvent was distilled away, and the residue was dried at 80° C. in vacuo for 8 hours to obtain a dark brown solid containing bis(ethylcyclopentadienyl)dichlorotantalum (Ta(EtCp)2Cl2). 1,060 ml of toluene was added to this dark brown solid, and the resulting mixture was ice-cooled. 187 ml (623 mmol) of a toluene solution (65 wt %) of sodium bis(2-methoxyethoxy)aluminum hydride was added dropwise to the mixture, and temperature was returned to room temperature, followed by stirring for 17 hours. 107 ml of water was added to the mixture, followed by stirring until foaming does not occur. Insoluble contents were filtered out, and the solvent was distilled away from the filtrate. 590 ml of hexane was added to the residue, the insoluble contents were filtered out. When the filtrate was cooled to −70° C., a white solid was formed. The supernatant was removed, and the solid was washed with 24 ml of cold pentane two times to obtain a solid. The solid obtained was distilled in vacuo at 2.5 Pa/100° C. to obtain 7.79 g (yield: 10.1%) of a colorless liquid. When this liquid was cooled to room temperature, white crystals were formed.

후처리

  1. additionwas added
  2. temperatureby refluxing for 1 hour
  3. distillationThe solvent was distilled away
  4. customthe residue was dried at 80° C. in vacuo for 8 hours
  5. customto obtain a dark brown solid
  6. temperaturecooled
  7. customwas returned to room temperature
  8. stirringby stirring until foaming
  9. filtrationInsoluble contents were filtered out
  10. distillationthe solvent was distilled away from the filtrate
  11. addition590 ml of hexane was added to the residue
  12. filtrationthe insoluble contents were filtered out
  13. customa white solid was formed
  14. customThe supernatant was removed
  15. washthe solid was washed with 24 ml of cold pentane two times
  16. customto obtain a solid
  17. customThe solid obtained
  18. distillationwas distilled in vacuo at 2.5 Pa/100° C.

출처 및 근거

ORD 기록
ord-2327e0ec2bd94b6fa557bbe927943378
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592471B2

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