Reaktion #941228

Reaktionsgleichung

(+)-6-(4-bromobenzyl)oxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochloride

toluene

ethanol

sodium carbonate

→

titled compound

(+)-2-[2-(N,N-Dimethylamino)ethyl]-6-(3′-formylbiphenyl-4-yl)methoxytetralin hydrochloride

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturunder reflux for 14 hr under argon
3. 3
   TemperaturAfter cooling
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with saturated aqueous sodium chloride
6. 6
   Sonstigedried
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by alumina column chromatography (eluent:ethyl acetate:hexan=1:20 to 1:2)
9. 9
   Sonstigewas then recrystallized from methanol-diisopropyl ether

Vorschrift

A mixture of (+)-6-(4-bromobenzyl)oxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochloride (1 g), toluene (20 ml), ethanol (2.5 ml), and 2 M aqueous sodium carbonate (2.5 ml) was stirred at room temperature for 10 min. 3-Formylbenzeneboric acid (460 mg) and tetrakis(triphenylphosphine) palladium (82 mg) were added and the reaction mixture was heated under reflux for 14 hr under argon. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent:ethyl acetate:hexan=1:20 to 1:2) and converted into its hydrochloride, which was then recrystallized from methanol-diisopropyl ether to obtain the titled compound (590 mg).

Quelle