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

HRID 601649
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 601649
[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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6362Isopropyl iodideHCID 12679HexamethylphosphoramideHCID 113677915-Bromo-1-oxoindeneHCID 178418244HCID 178418244, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-29960a3fe73d4452940101a44302149c
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902369B2

Notizen zur Reaktion

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