反应 #7045

反应方程式

1-(2-chloroethyl)-pyrrolidine hydrochloride

Potassium carbonate

sodium iodide

3-methyl-2-nitrophenol

1-(2-chloroethyl)-pyrrolidine hydrochloride

potassium carbonate

→

1-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine

收率 69.0%

反应条件

后处理

1. 1
   workup.ADDITIONwere added
2. 2
   温度After an additional hour of reflux
3. 3
   洗涤was washed with sequentially with water (1×100 mL) and brine (1×100 mL.) The combined organic fractions
4. 4
   其他spontaneously crystallized
5. 5
   其他the solid was purified by flash chromatography (5% MeOH in CH2Cl2)

实验过程

Potassium carbonate (34.9 g., 252 mmol) and sodium iodide (1.0 g., 6.5 mmol) were added to a solution of 3-methyl-2-nitrophenol (10 g., 65.3 mmol). With stirring, 1-(2-chloroethyl)-pyrrolidine hydrochloride (16.65 g., 98 mmol) was added portion-wise to the solution. The reaction mixture was refluxed for 15 hours, at which time 1-(2-chloroethyl)-pyrrolidine hydrochloride (8.5 g., 50 mmol) and potassium carbonate (18 g., 130 mmol) were added. After an additional hour of reflux, the reaction mixture was allowed to cool to room temperature and was washed with sequentially with water (1×100 mL) and brine (1×100 mL.) The combined organic fractions spontaneously crystallized, and the solid was purified by flash chromatography (5% MeOH in CH2Cl2) to give 1-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine (10.291 g., 69%). MS: 251 (M+H)+

来源