HCID 67336197, Verbindung → 1-(6-Methoxy-4-methylpyridin-3-yl)propan-1-one

HRID 1671321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1671321
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:12])[CH2:10][CH3:11])=[C:5]([CH3:13])[CH:4]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[C:5]([CH3:13])[CH:4]=1

Komponenten

4

Edukt 1

HCID 67336197HCID 67336197, Verbindung

Produkt 1

HCID 673357591-(6-Methoxy-4-methylpyridin-3-yl)propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(6-methoxy-4-methyl-pyridin-3-yl)-propan-1-ol (445 mg, 2.45 mmol, 1 eq.) in CHCl3 (10 ml) is added activated manganese dioxide (4.3 g, 49 mmol, 20 eq.) in one portion at RT. The reaction mixture is heated at reflux for 48 h. After cooling to RT, the mixture is filtered through Celite® (filter material) and concentrated under reduced pressure. The resulting crude residue is purified by column chromatography on silica gel eluting with 10% EtOAc/iso-hexane to yield 1-(6-methoxy-4-methyl-pyridin-3-yl)-propan-1-one as a white solid. MS: m/z 180.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 1.2 (t, 3H), 2.55 (s, 3H), 2.95 (q, 2H), 4.00 (s, 3H), 6.60 (s, 1H), 8.65 (s, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 48 h
  3. filtrationthe mixture is filtered through Celite® (filter material)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude residue is purified by column chromatography on silica gel eluting with 10% EtOAc/iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-2f14d0411c8e4348b7f1aa3853490e95
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994203B2

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