Реакция #86489

Уравнение реакции

EtOAc brine

Potassium carbonate

4-amino-3-nitrophenol

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

→

title compound

Выход 38.2%

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

Выход 38.2%

Растворители

DMF

Условия реакции

Обработка

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

Методика

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).

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