反应详情

温度

0 °C

2-Chloromethylbenzoyl chloride (18.90 g, 0.1 mol) was dissolved in dichloromethane (50 ml). The solution was added to a mixture of methoxyamine hydrochloride (12.53 g, 0.15 mol), pyridine (19.78 g, 0.25 mol) and dry dichloromethane (150 ml) under ice-cooling over 1 hour, and then the resulting mixture was stirred at 0° C. for 2 hours. After completion of the reaction, water (300 ml) was added, adjusted to pH<2 with conc. hydrochloric acid, and extracted with dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in dichloromethane (200 ml), and phosphorus pentachloride (20.82 g, 0.1 mol) was added under ice-cooling over 5 minutes. The mixture was stirred at 0° C. for 1 hour. After completion of the reaction, saturated aqueous sodium bicarbonate solution (400 ml) was added, and the mixture was extracted with dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-chloromethyl-α-methoxyiminobenzyl chloride (18.15 g, 83.2%) as a colorless oil.

1. temperaturecooling over 1 hour
2. additionwas added
3. extractionextracted with dichloromethane
4. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in dichloromethane (200 ml)
7. temperaturecooling over 5 minutes
8. stirringThe mixture was stirred at 0° C. for 1 hour
9. additionwas added
10. extractionthe mixture was extracted with dichloromethane
11. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
12. concentrationconcentrated under reduced pressure
13. customthe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)