Dimethylformamide → 6-(2-Pyridyl)-methyloxy-2-acetylnaphthalene

HRID 233764

Reaktionsgleichung

Reaktionsgleichung von HRID 233764
O[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](=[O:14])[CH3:13])[CH:6]=[CH:5]2.[H-].[Na+].Cl.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1CCl.CN([CH:29]=[O:30])C>>[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:30][CH3:29])=[C:7]([C:12](=[O:14])[CH3:13])[CH:6]=[CH:5]2

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 23392Picolyl chloride hydrochlorideHCID 24758Sodium hydrideHCID 826311-(6-Hydroxy-2-naphthyl)ethan-1-one

Produkt 1

HCID 233569346-(2-Pyridyl)-methyloxy-2-acetylnaphthaleneAusbeute 75,5 %

Versuchsvorschrift

To a solution of 6-hydroxy-2-acetylnaphthalene (1.04 g) in DMF (20 ml) were added sodium hydride (60%, 0.65 g) and 2-picolyl chloride hydrochloride (1.28 g) under ice-cooling and the resultant-mixture was stirred at room temperature for 12 hours. The reaction mixture was partitioned between toluene and water. The organic layer was washed with a saturated saline solution and dried over anhydrous magnesium sulfate. After concentration in vacuo, the residue was subjected to column chromatography on silica gel eluting with ethyl acetate/hexane to obtain the title compound (1.17 g, yield =75.5%). The NMR spectrum is as follows.

Aufarbeitung

  1. temperaturecooling
  2. customThe reaction mixture was partitioned between toluene and water
  3. washThe organic layer was washed with a saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter concentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2f56598a329a4ed4b113a669773b9a55
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594016

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