Water → 9-n-Hexylfluorene

HRID 1353028

반응식

HRID 1353028 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.C([Li])CCC.[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].O>C1COCC1>[CH2:19]([CH:12]1[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)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

참가 물질

6

반응물 4

HCID 962WaterHCID 6853FluoreneHCID 81011-BromohexaneHCID 178418339Butyllithium

생성물 1

HCID 64278799-n-Hexylfluorene수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-50 °C

실험 절차

To a solution of fluorene (33.2 g, 0.20 mol) in 300 mL THF at −78° C., n-butyllithium (2.5 M, 80 mL) was added dropwisely. The mixture was stirred at −50° C. for 45 minutes, and then cooled to −78° C. again and n-hexylbromide (33.0 g, 0.20 mol) in THF (25 mL) was added dropwise to the mixture. The solution was allowed to warm up to room temperature and stirred for 5 h. The mixture was then poured into water and extracted with ether. The organic extracts were washed with brine and dried over magnesium sulfate, and purified by silica gel column with hexane to give pure compound 2 (38 g, yield 76%).

후처리

  1. temperaturecooled to −78° C. again
  2. temperatureto warm up to room temperature
  3. stirringstirred for 5 h
  4. extractionextracted with ether
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. custompurified by silica gel column with hexane

출처 및 근거

ORD 기록
ord-55fc9f89819045189c01112a2f99cb05
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220819B2

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