Water → 9-n-Hexylfluorene

HRID 1353028

反応式

HRID 1353028 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 6853FluoreneHCID 81011-BromohexaneHCID 178418339Butyllithium

生成物 1

HCID 64278799-n-Hexylfluorene収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-50 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-55fc9f89819045189c01112a2f99cb05
出典データセット
uspto-grants-2007_05
特許番号
US07220819B2

関連ノート

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