Reaktion #62694

Reaktionsgleichung

4-(2-Tetrahydropyran-2-yloxyethyl)phenol

4-(2-tetrahydropyran-2-yloxyethyl)phenol

2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-bromopropoxycarbonyl)-1,4-dihydropyridine

K2CO3

→

2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated
2. 2
   Temperaturat reflux overnight
3. 3
   TemperaturAfter cooling
4. 4
   Filtrationthe solid was filtered
5. 5
   Sonstigethe solvent removed under reduced pressure
6. 6
   WaschenThe organic layer was washed with 10% NaOH (2×100 mL) and water (2×100 mL)
7. 7
   Trocknendried over sodium sulfate
8. 8
   SonstigeThe solvent was evaporated under reduced pressure
9. 9
   Sonstigeto provide an oil which
10. 10
    Sonstigewas purified by flash chromatography (EtOAc: CH2Cl2 --15:85)

Vorschrift

4-(2-Tetrahydropyran-2-yloxyethyl)phenol (9, 72.1 g, 0.32 mol) was added to a solution of 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-bromopropoxycarbonyl)-1,4-dihydropyridine (12, 105 g, 0.23 mol) and K2CO3 (48 g, 0.35 mol) in acetone (700 mL), and the mixture heated at reflux overnight. After cooling, the solid was filtered, the solvent removed under reduced pressure, and the residue solubilised in CH2Cl2 (1 L). The organic layer was washed with 10% NaOH (2×100 mL) and water (2×100 mL) and dried over sodium sulfate. The solvent was evaporated under reduced pressure to provide an oil which was purified by flash chromatography (EtOAc: CH2Cl2 --15:85) to yield 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine (1, mp<50° C.).

Quelle