反应详情

温度

80 °C

Dichloroethane (50 ml), thionyl chloride (6.54 g, 0.055 mol) and N,N-dimethylformamide (0.25 ml) were added to 2-phenoxymethylbenzoic acid (11.41 g, 0.05 mol), and the mixture was stirred at 80° C. for 2 hours. After completion of the reaction, the mixture was concentrated under reduced pressure, and the residue was dissolved in dichloromethane (25 ml). The solution was added to a mixture of ethoxyamine hydrochloride (5.85 g, 0.06 mol), pyridine (9.89 g, 0.125 mol) and dry dichloromethane (50 ml) under ice-cooling over 20 minutes, and then the resulting mixture was stirred at room temperature for 2 hours. After completion of the reaction, water (200 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. Acetonitrile (150 ml), triphenylphosphine (20.98 g, 0.08 mol) and carbon tetrachloride (24.61 g, 0.16 mol) were added to the residue, and the mixture was stirred under reflux for 1.5 hours. After completion of the reaction, the mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give α-ethoxyimino-2-phenoxymethylbenzyl chloride (13.51 g, 93.2%) as a colorless oil.

1. customAfter completion of the reaction
2. concentrationthe mixture was concentrated under reduced pressure
3. dissolutionthe residue was dissolved in dichloromethane (25 ml)
4. temperaturecooling over 20 minutes
5. stirringthe resulting mixture was stirred at room temperature for 2 hours
6. additionwas added
7. extractionextracted with dichloromethane
8. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. stirringthe mixture was stirred
11. temperatureunder reflux for 1.5 hours
12. customAfter completion of the reaction
13. concentrationthe mixture was concentrated under reduced pressure
14. customthe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)