Reaktion #470148

Reaktionsgleichung

sodium chloride

sodium carbonate

4-methoxyphenylboric acid

6-(4-Bromobenzyl)oxy-2-(N,N-dimethylamino)methyltetralin

→

hydrochloride

2-(N,N-Dimethylamino)methyl-6-(4′-methoxybiphenyl-4-yl)methoxytetralin Hydrochloride

Lösungsmittel

ethanol

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturunder reflux for 6 hours in an argon atmosphere
3. 3
   Extraktionwas then extracted with ethyl acetate
4. 4
   SonstigeThe organic layer was dried
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/10)

Vorschrift

6-(4-Bromobenzyl)oxy-2-(N,N-dimethylamino)methyltetralin (374 mg; obtained in Reference Example 33) and tetrakis-(triphenylphosphine) palladium (35 mg) were dissolved in toluene (8 ml), to which were added an ethanol solution (1 ml) of 4-methoxyphenylboric acid (198 mg) and an aqueous 2 M sodium carbonate solution (1 ml). The reaction mixture was heated under reflux for 6 hours in an argon atmosphere. A saturated aqueous sodium chloride solution was added to this, which was then extracted with ethyl acetate. The organic layer was dried, and then concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/10), and then processed with 4 N hydrochloric acid-ethyl acetate to form a hydrochloride. The thus-formed salt was recrystallized from ethanol-ethyl acetate to obtain the entitled compound (0.290 g).

Quelle