Water → 9,9-dihexylfluorene

HRID 1368785노트

반응식

HRID 1368785 반응식
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH2:20](Br)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].O>O1CCCC1>[CH2:14]([C:12]1([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

참가 물질

6

반응물 4

HCID 962WaterHCID 6853FluoreneHCID 8058Hexane2회HCID 81011-Bromohexane2회

생성물 1

HCID 51284499,9-dihexylfluorene수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In the stream of dry nitrogen, 5.0 g (30 mmol) of fluorene was dissolved in dry tetrahydrofuran. To this solution, 22 m l (35 mmol) of a 1.6 M hexane solution of n-butylithium was added dropwise at −78° C., and the mixture was stirred at the temperature for 1 hour. To this was then added dropwise 4.9 ml (35 mmol) of n-hexyl bromide, and the mixture was stirred at −78° C. for 1 hour, and then at room temperature for 1 hour. To the resultant, 22 ml (35 mmol) of a 1.6 M hexane solution of n-butylithium was further added dropwise at −78° C., and the mixture was stirred at the temperature for 1 hour. To this was then added dropwise 4.9 ml (35 mmol) of n-hexyl bromide, and the mixture was stirred at −78° C. for 1 hour, and then at room temperature for 1 hour. Water was added dropwise to this mixture with ice-cooling, and the resultant was then subjected to extraction with ethyl acetate. The extract was dehydrated and dried over magnesium sulfate, and the solvent was then distilled off. The residue was subjected to recrystallization from hexane to obtain 9.5 g (95%) of 9,9-dihexylfluorene.

후처리

  1. stirringthe mixture was stirred at −78° C. for 1 hour
  2. waitat room temperature for 1 hour
  3. stirringthe mixture was stirred at the temperature for 1 hour
  4. stirringthe mixture was stirred at −78° C. for 1 hour
  5. waitat room temperature for 1 hour
  6. temperaturecooling
  7. extractionthe resultant was then subjected to extraction with ethyl acetate
  8. dry with materialdried over magnesium sulfate
  9. distillationthe solvent was then distilled off
  10. customThe residue was subjected to recrystallization from hexane

출처 및 근거

ORD 기록
ord-f6434f57df964e3c8c585f3933a0505c
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573650B2

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