2,7-Di-tert-butylfluorene → 1-(3-Butylcyclopentadien-1-yl)-1-(2,7-di-tert-butylfluoren-9-yl)-1,1-diphenylmethane

HRID 476289노트

반응식

HRID 476289 반응식
[C:1]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Li][CH2:23][CH2:24][CH2:25][CH3:26]>CCOCC.CCCCCCC>[CH2:23]([C:24]1[CH:23]=[C:23]([C:24]([CH:8]2[C:7]3[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][C:11]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:13]=3)([C:5]2[CH:17]=[CH:16][CH:15]=[CH:7][CH:6]=2)[C:25]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:26]=2)[CH2:26][CH:25]=1)[CH2:24][CH2:25][CH3:26]

참가 물질

5

반응물 2

HCID 40900822,7-Di-tert-butylfluoreneHCID 178418339Butyllithium

생성물 1

HCID 866291471-(3-Butylcyclopentadien-1-yl)-1-(2,7-di-tert-butylfluoren-9-yl)-1,1-diphenylmethane수율 171.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8900Heptane용매

실험 절차

To 2,7-di-tert-butylfluorene (15 g, 54 mmol) dissolved in Et2O (100 mL) was added n-BuLi (5.8 mL of 10 M in hexanes, 58 mmol) at 0° C. The mixture was warmed to room temperature and stirred overnight. The anion solution was added to 2-butyl-6,6-diphenylpentafulvene (F-1) (16 g, 56 mmol) dissolved in Et2O (100 mL) at −78° C. in 5 minutes. The mixture was warmed to room temperature and stirred for 2 days. The reaction was quenched with a mixture of ice and 10% HCl aqueous solution. The mixture was extracted with Et2O. The organic layer was washed with water and dried over anhydrous sodium sulfate. Removal of the solvent under vacuum gave a viscous oil. The oil was stirred in heptane to give a white solid. The solid was filtered, washed with heptane and dried under vacuum. A mixture of isomers for the desired product (18.7 g, 61.3% yield) was obtained as a white solid.

후처리

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for 2 days
  3. customThe reaction was quenched with a mixture of ice and 10% HCl aqueous solution
  4. extractionThe mixture was extracted with Et2O
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customRemoval of the solvent under vacuum
  8. customgave a viscous oil
  9. customto give a white solid
  10. filtrationThe solid was filtered
  11. washwashed with heptane
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-2f6a607662944eaf9f5d96f1c456ea22
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637691B2

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