تفاعل #86489

معادلة التفاعل

EtOAc brine

Potassium carbonate

4-amino-3-nitrophenol

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

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title compound

المردود 38.2%

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

المردود 38.2%

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر