Reaktion #2027734

Reaktionsgleichung

1-(pyridin-4-yl)-2-(furan-2-yl)ethene

ammonium formate

→

title compound

Ausbeute 31.0%

1-(Pyridin-4-yl)-2-(furan-2-yl)ethane

Ausbeute 31.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for five hours
2. 2
   FiltrationThe catalyst was filtered off
3. 3
   Sonstigethe solvent evaporated
4. 4
   SonstigeThe residue was partitioned between dichloromethane and water
5. 5
   SonstigeThe organic layer was separated
6. 6
   Trocknendried (MgSO4)
7. 7
   Sonstigeevaporated
8. 8
   Sonstigeto give a beige oil
9. 9
   SonstigeThis material was chromatographed on silica gel with a gradient of ethyl acetate in hexane (50%-100%) as eluant

Vorschrift

A solution of 1-(pyridin-4-yl)-2-(furan-2-yl)ethene (8 g, 46.8 mmol) in methanol (200 ml) was treated with ammonium formate (14.7 g, 234.0 mmol). 10% Palladium on charcoal catalyst (400 mg, 5% (w/w)) was added and the mixture was stirred at reflux for five hours. The catalyst was filtered off and the solvent evaporated. The residue was partitioned between dichloromethane and water. The organic layer was separated, dried (MgSO4) and evaporated to give a beige oil. This material was chromatographed on silica gel with a gradient of ethyl acetate in hexane (50%-100%) as eluant to afford the title compound as a colourless oil (2.5 g, 31%); δH (DMSO-d6) 2.94-3.06 (4H, m, 2×CH2), 6.06-6.12 (1H, m, furanyl H), 6.32-6.38 (1H, m, furanyl H), 7.20-7.28 (2H, m, pyridinyl H), 7.50-7.56 (1H, m, furanyl H), and 8.40-8.50 (2H, m, pyridinyl H).

Quelle