反应 #40262

反应方程式

2-chloro-1-methylpyridinium iodide

(1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid

triethylamine

2-iodo-6-methoxyaniline

→

2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide

收率 89.6%

2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxyphenyl)acetamide

收率 89.6%

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度The reaction mixture is heated
2. 2
   温度at reflux for 20 hours
3. 3
   温度After cooling
4. 4
   萃取acidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane
5. 5
   洗涤The organic phases are washed with saturated aqueous sodium chloride solution
6. 6
   干燥dried over magnesium sulfate
7. 7
   其他evaporated under vacuum
8. 8
   其他Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6)

实验过程

A solution of (1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid (567 mg; 2.86 mmol; 1 eq) (7) and 2-iodo-6-methoxyaniline (1 g; 2.86 mmol; 1 eq) in anhydrous dichloromethane (30 mL) is admixed with 2-chloro-1-methylpyridinium iodide (1.46 g; 5.73 mmol; 2 eq) and triethylamine (3.98 mL; 28.65 mmol; 10 eq). The reaction mixture is heated at reflux for 20 hours. After cooling and acidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane. The organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated under vacuum. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6) gives 1.10 g of 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide (16) in the form of a yellow foam (yield: 90%).

来源