Potassium Permanganate → HCID 17977726, Verbindung

HRID 274433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274433
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[OH:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=O.[K+]>O>[N:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:17]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:14]([O:15][CH3:16])[CH:13]=2)=[O:18])[CH:20]=1

Komponenten

4

Edukt 2

HCID 516875Potassium Permanganate2×HCID 13365804alpha-[4-(Benzyloxy)-3-methoxyphenyl]-3-pyridinemethanol

Produkt 1

HCID 17977726HCID 17977726, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

ba) 3.2 g of alpha-[4-(benzyloxy)-5-methoxyphenyl]-3-pyridinemethanol suspended in 50 ml of water are treated with 2.5 g of potassium permanganate, whereupon the mixture is stirred at 90° for 30 minutes After adding a further 1.0 g of potassium permanganate and stirring for a further 30 minutes at 90° the mixture is cooled to room temperature and extracted twice with 150 ml of ethyl acetate each time. The combined ethyl acetate phases are washed with sodium chloride solution, dried over sodium sulfate and evaporated. The thus-obtained residue is chromatographed on 50 g of silica gel with ethyl acetate. After recrystallization from methylene chloride/hexane there is obtained 4-(benzyloxy)-3-methoxyphenyl 3-pyridyl ketone of m.p. 76°.

Aufarbeitung

  1. stirringstirring for a further 30 minutes at 90° the mixture
  2. extractionextracted twice with 150 ml of ethyl acetate each time
  3. washThe combined ethyl acetate phases are washed with sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe thus-obtained residue is chromatographed on 50 g of silica gel with ethyl acetate
  7. customAfter recrystallization from methylene chloride/hexane there

Quellen und Nachweise

ORD-Eintrag
ord-8cbba5fcbe45472ea4509943df71f92a
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389653

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