Water → N-(Hex-5-enyl)phthalimide

HRID 361474

Reaktionsgleichung

Reaktionsgleichung von HRID 361474
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[K].O>CS(C)=O>[CH2:2]([N:12]1[C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]2[C:8]1=[O:18])[CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7]

Komponenten

5

Edukt 3

HCID 962WaterHCID 759066-Bromo-1-hexeneHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 12422290N-(Hex-5-enyl)phthalimideAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

This example illustrates a synthesis of N-(5,6-Oxidohexyl)phthalimide (inventive compound no. 1103). 1-bromo-5-hexene (6.52 g, 40 mmol) was added to a potassium phthalimide (7.4 g, 40 mmol) suspension in 50 mL of dimethyl sulfoxide and stirred overnight. After 12 hours of stirring at room temperature, the reaction was poured into a separatory funnel containing 300 mL of water and extracted with dichloromethane (5×200 mL). The organic extracts were combined, washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel (eluant: 10% acetone/hexane) to yield 9.2 g (100% yield) of N-(5-Hexenyl)phthalimide (inventive compound no. 1101).

Aufarbeitung

  1. stirringAfter 12 hours of stirring at room temperature
  2. additionthe reaction was poured into a separatory funnel
  3. extractionextracted with dichloromethane (5×200 mL)
  4. washwashed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product obtained
  8. customwas further purified by flash chromatography over silica gel (eluant: 10% acetone/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-99f0c994954d46a59fcb29e44f25afb9
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866576

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