반응 #49361

반응 방정식

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

수율 84.0%

용매

water

methanol

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate
2. 2
   세척The organic layer was washed with saturated brine
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   기타The solvent was evaporated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (190 mL)
6. 6
   온도cooling
7. 7
   온도Then, 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
    추출extracted with chloroform
11. 11
    세척The organic layer was washed with saturated brine
12. 12
    건조dried over anhydrous sodium sulfate
13. 13
    기타The solvent was evaporated under reduced pressure
14. 14
    기타The residue was purified by flash column chromatography (chloroform/methanol=100/0, 99/1)

실험 절차

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%).

출처