反応 #49361

反応方程式

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

収率 84.0%

溶媒

water

methanol

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate
2. 2
   洗浄The organic layer was washed with saturated brine
3. 3
   乾燥dried over anhydrous sodium sulfate
4. 4
   その他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
    抽出extracted with chloroform
11. 11
    洗浄The organic layer was washed with saturated brine
12. 12
    乾燥dried over anhydrous sodium sulfate
13. 13
    その他The solvent was evaporated under reduced pressure
14. 14
    その他The residue was purified by flash column chromatography (chloroform/methanol=100/0, 99/1)

実験手順

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%).

出典