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Fluorene → HCID 15045041、化合物

HRID 440343
ノート
印刷プレビュー

反応式

HRID 440343 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.Br[CH2:20][CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1.CCCCCC.C(OCC)(=O)C>C1COCC1>[CH:1]1[C:13]2[CH:12]([CH2:20][CH2:21][CH:22]3[O:26][CH2:25][CH2:24][O:23]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6853FluoreneHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 21226206Ethyl acetate hexaneHCID 178418339Butyllithium

生成物 1

HCID 15045041HCID 15045041、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

2-(9-Fluorenyl)ethyl-1,3-dioxolane was prepared from a solution of fluorene (30.0 g, 180.5 mmol) in 400 ml of dry THF cooled in a -78° C. bath under argon, to which was added 100 ml of n-butyllithium (2.0M in cyclohexane) over 15 minutes After stirring for 0.5 hours at 78° C. 2-(2-bromoethyl)-1, 3-dioxolane (22.3 ml, 190 mmol) was added dropwise, and the resulting solution stirred at room temperature for 16 hours. Concentration in vacuo yielded an orange residue which was partitioned between ethyl acetate and saturated ammonium chloride. The organic layer was then washed with brine, dried with magnesium sulfate, and concentrated in vacuo to afford an orange oil. Flash chromatography on silica, hexane:ethyl acetate 20:1 to 1:1 yielded a yellow oil (36.38 g, 76%).

後処理

  1. stirringthe resulting solution stirred at room temperature for 16 hours
  2. concentrationConcentration in vacuo
  3. customyielded an orange residue which
  4. customwas partitioned between ethyl acetate and saturated ammonium chloride
  5. washThe organic layer was then washed with brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford an orange oil

出典と根拠

ORDレコード
ord-368a5c9bc3f34386b6f90389a02404a4
出典データセット
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05519043

反応ノート

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