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Hexane → 2-(3-Tert-butylcyclopentadienyl)-3-(3,6-di-tert-butylfluorenyl)pentane

HRID 495762
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HRID 495762 반응식
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:11]=3)([CH3:4])([CH3:3])[CH3:2].[CH3:22]CCCCC.C([Li])CCC.[C:33]([C:37]1[CH:38]=[CH:39][C:40](=[C:42]([CH2:45]C)[CH2:43][CH3:44])[CH:41]=1)([CH3:36])([CH3:35])[CH3:34]>C1COCC1.CCOCC.O>[C:33]([C:37]1[CH:38]=[CH:39][CH:40]([CH:42]([CH:43]([C:11]2[C:10]3[CH2:9][C:8]4[C:16](=[CH:17][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=4)[C:15]=3[CH:14]=[C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=2)[CH2:44][CH3:22])[CH3:45])[CH:41]=1)([CH3:34])([CH3:35])[CH3:36]
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참가 물질

8

반응물 4

HCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 178181433-Tert-butyl-6,6-diethylfulveneHCID 178418339Butyllithium

생성물 1

HCID 1317251382-(3-Tert-butylcyclopentadienyl)-3-(3,6-di-tert-butylfluorenyl)pentane수율 70.3%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 3283Diethyl Ether용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 1.99 g (7.1 mmol) of 3,6-di-tert-butylfluorene in 30 ml of THF, 4.6 ml (7.5 mmol) of a hexane solution of n-butyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. To the resulting red solution, a solution of 1.50 g (7.9 mmol) of 3-tert-butyl-6,6-diethylfulvene in 30 ml of THF was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 100 ml of ether, 50 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was isolated and purified by column chromatography (silica gel, developing solvent: hexane) to obtain 2.34 g (4.99 mmol) of a white solid (yield: 70%). The analyzed values are given below.

후처리

  1. stirringby stirring at room temperature for one night
  2. additionwas added
  3. washThe separated organic phase was washed with water
  4. dry with materiala saturated saline solution, then dried over magnesium sulfate
  5. filtrationfiltered
  6. customFrom the filtrate, the solvent was removed under reduced pressure
  7. customto obtain a liquid
  8. customThe liquid was isolated
  9. custompurified by column chromatography (silica gel, developing solvent: hexane)

출처 및 근거

ORD 기록
ord-f5874959c87c48bd90b0eceeb9bf4a08
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06939928B1

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