Reaktion #86489

Reaktionsgleichung

EtOAc brine

Potassium carbonate

4-amino-3-nitrophenol

2-(2-bromoethoxy)tetrahydro-2H-pyran

→

title compound

Ausbeute 38.2%

2-nitro-4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)aniline

Ausbeute 38.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITfor 3 days at room temperature
2. 2
   ExtraktionThe aqueous layer was extracted twice with EtOAc
3. 3
   WaschenThe combined organic layer was washed with brine three times
4. 4
   Trocknendried over MgSO4
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe resulting material was purified by flash chromatography on silica eluting with 5% to 40% EtOAc/Hexane

Vorschrift

4-amino-3-nitrophenol (2.0 g, 12.977 mmol) was dissolved in DMF (20 ml) and Potassium carbonate (3.59 g, 25.953 mmol) was added. To the mixture was added 2-(2-bromoethoxy)tetrahydro-2H-pyran (2.55 ml, 16.87 mmol) and the reaction mixture was stirred at 50° C. for 6 hours and then for 3 days at room temperature. The reaction mixture was poured into EtOAc/brine. The aqueous layer was extracted twice with EtOAc. The combined organic layer was washed with brine three times, dried over MgSO4 and evaporated. The resulting material was purified by flash chromatography on silica eluting with 5% to 40% EtOAc/Hexane to afford title compound (1.4 g, yield: 38%). 1H-NMR (400 MHz, CDCl3) δ 1.51-1.68 (m, 4H) 1.71-1.89 (m, 2H) 3.46-3.61 (m, 1H) 3.72-3.99 (m, 2H) 4.03-4.24 (m, 3H) 4.64-4.79 (m, 1H) 6.78 (d, 1H) 7.09-7.17 (m, 1H) 7.60 (d, 1H).

Quelle