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Isopropyl iodide → 5-Bromo-2-isopropyl-1-oxoindane

HRID 601649
ノート
印刷プレビュー

反応式

HRID 601649 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]=[CH:5]2.CN(C)P(N(C)C)(N(C)C)=O.[CH3:23][CH2:24][CH2:25]CCC.C([Li])CCC.C(I)(C)C>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([CH:24]([CH3:25])[CH3:23])[CH2:5]2
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

7

反応物 4

HCID 6362Isopropyl iodideHCID 12679HexamethylphosphoramideHCID 113677915-Bromo-1-oxoindeneHCID 178418244HCID 178418244、化合物

生成物 1

HCID 231583405-Bromo-2-isopropyl-1-oxoindane

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
-78 °C

実験手順

Under nitrogen atmosphere, 100 mg of 5-bromo-1-oxoindene was dissolved in 2 ml of tetrahydrofuran, and cooled down to −78° C. 0.4 ml of hexamethylphosphoramide, 0.3 ml of 1.57 M n-butyllitium hexane solution, and 1.0 ml of isopropyl iodide were added, and the mixture was stirred at −78° C. for 2 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by preparative thin-layer chromatography (ethyl acetate/hexane=1/2) to obtain 26 mg of the above compound as a white solid.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washEthyl acetate layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationThe solvents were distilled outunder reduced pressure
  5. customthe residues were separated
  6. custompurified by preparative thin-layer chromatography (ethyl acetate/hexane=1/2)

出典と根拠

ORDレコード
ord-29960a3fe73d4452940101a44302149c
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902369B2

反応ノート

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