反应 #49361

反应方程式

diisopropylethylamine

chloromethyl methyl ether

hydrochloric acid water

sodium hydroxide

diisopropylethylamine

chloromethyl methyl ether

3-Acetoxy-N-(1-methyl-1-phenylethyl)benzamide

→

3-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamide

收率 84.0%

溶剂

water

methanol

反应条件

后处理

1. 1
   萃取extracted with ethyl acetate
2. 2
   洗涤The organic layer was washed with saturated brine
3. 3
   干燥dried over anhydrous sodium sulfate
4. 4
   其他The solvent was evaporated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (190 mL)
6. 6
   温度cooling
7. 7
   温度Then, the reaction mixture was warmed to room temperature
8. 8
   workup.STIRRINGstirred for 2 hours
9. 9
   workup.STIRRINGby further stirring for 2 hours
10. 10
    萃取extracted with chloroform
11. 11
    洗涤The organic layer was washed with saturated brine
12. 12
    干燥dried over anhydrous sodium sulfate
13. 13
    其他The solvent was evaporated under reduced pressure
14. 14
    其他The residue was purified by flash column chromatography (chloroform/methanol=100/0, 99/1)

实验过程

3-Acetoxy-N-(1-methyl-1-phenylethyl)benzamide (9.57 g, 32.2 mmol) was dissolved in methanol (190 mL), and the solution was added with 4 mol/L sodium hydroxide solution (32.2 mL), followed by stirring at room temperature for 20 minutes. The reaction mixture was added with 1 mol/L hydrochloric acid water to adjust the pH to 7, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane (190 mL), and the solution was added with diisopropylethylamine (16.8 mL, 96.6 mmol) and chloromethyl methyl ether (3.70 mL, 48.3 mmol) under ice-cooling. Then, the reaction mixture was warmed to room temperature and stirred for 2 hours. The mixture was added with diisopropylethylamine (5.60 mL, 32.2 mmol) and chloromethyl methyl ether (1.20 mL, 15.8 mmol), followed by further stirring for 2 hours. The reaction mixture was added with water and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (chloroform/methanol=100/0, 99/1) to obtain 3-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamide (8.09 g, yield 84%).

来源