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

HRID 270986

반응식

HRID 270986 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].CCCCCC.C([Li])CCC.[C:33]([C:37]1[CH:38]=[CH:39][C:40](=[C:42]([CH3:44])[CH3:43])[CH:41]=1)([CH3:36])([CH3:35])[CH3:34]>CCOCC.O>[C:33]([C:37]1[CH:38]=[CH:39][CH:40]([C:42]([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)([CH3:44])[CH3:43])[CH:41]=1)([CH3:36])([CH3:35])[CH3:34]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 146882832-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-dieneHCID 178418339Butyllithium

생성물 1

HCID 1317251212-(3-Tert-butylcyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propane수율 43.1%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of 1.98 g (7.1 mmol) of 3,6-di-tert-butylfluorene in 40 ml of ether, 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 1.56 g (9.6 mmol) of 3-tert-butyl-6,6-dimethylfulvene in 20 ml of ether was further dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 60 ml of water was added. The separated organic phase was dried over magnesium sulfate and then filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid was purified by column chromatography (silica gel, developing solvent: hexane) to obtain 1.35 g of a light yellow solid (yield: 43%). The analyzed values are given below.

후처리

  1. stirringby stirring at room temperature for one night
  2. dry with materialThe separated organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customFrom the filtrate, the solvent was removed under reduced pressure
  5. customto obtain a solid
  6. customThe solid was purified by column chromatography (silica gel, developing solvent: hexane)

출처 및 근거

ORD 기록
ord-b6650b087f9742b3899941e4f6965496
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449533B2

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