Water → 1-[4-(2-Iodoethyl)phenyl]-5-phenylpentan-1-one

HRID 1795706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795706
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:21])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.[I-:22].[Na+].O>CC(=O)CC>[I:22][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:21])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 5238Sodium IodideHCID 221784791-[4-(2-Bromoethyl)phenyl]-5-phenylpentan-1-one

Produkt 1

HCID 221784841-[4-(2-Iodoethyl)phenyl]-5-phenylpentan-1-oneAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A solution of 1-[4-(2-bromoethyl)phenyl]-5-phenylpentan-1-one (18.2 g) and sodium iodide (9.5 g) in 2-butanone (180 ml) was stirred at 60° C. for 3.5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure to give a brown oily substance (19.2 g). The obtained brown oily substance was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=20:1) to give 1-[4-(2-iodoethyl)phenyl]-5-phenylpentan-1-one (17.2 g) as a yellow oily substance.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customto give a brown oily substance (19.2 g)
  6. customThe obtained brown oily substance was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-8a991819f10c407183ee3e11571e4ef0
Quelldatensatz
uspto-grants-2006_04
Patentnummer
USRE039072E1

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