Diethyl Ether → 4-(2-Methylbenzoyl)pyridine

HRID 2106663

Reaktionsgleichung

Reaktionsgleichung von HRID 2106663
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)[OH:20].C(OCC)C>ClCCl>[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)=[O:20]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 4385350(2-Methylphenyl)(4-pyridinyl)methanolHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 199571624-(2-Methylbenzoyl)pyridineAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Pyridinium chlorochromate (9.29 g, 43.1 mmol) was dissolved in dichloromethane (50 ml) and a solution of 2-methylphenyl-(4-pyridyl)methanol (5.72 g, 28.7 mmol) in dichloromethane (30 ml) was added. The reaction mixture became dark immediately, and was stirred for 2 h at room temperature. Diethyl ether (350 ml) was added, and the reaction mixture was filtered through "hyflo" and evaporated to a dark oil (11.26 g). Flash chromatography on silica gel (Merck Art 9385) eluting with heptane/tetrahydrofuran (4:1) provided the title compound (2.74 g, 48%) as an oil. T.l.c. rf=0.45 (SiO2, ethyl acetate).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered through "hyflo"
  2. customevaporated to a dark oil (11.26 g)
  3. washFlash chromatography on silica gel (Merck Art 9385) eluting with heptane/tetrahydrofuran (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-4dbfe014e07b4430a1f447e3f3a10fee
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04931450

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