反应详情

A solution of 2-hydroxymethyl-α-methoxy-N-methyl-phenylacetamide (0.42 g, 2.0 mmol) in tetrahydrofuran (4 ml) was stirred at 0° C., and thionyl chloride (0.17 ml, 2.4 mmol) and one drop of N,N-dimethylformamide were added. The mixture was stirred at room temperature for 2 hours, and water was added. The resulting mixture was extracted with ether, washed with saturated brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude product (0.38 g) as an oil. Benzaldehyde oxime (0.37 g, 3.1 mmol) and potassium carbonate (0.55 g, 4.0 mmol) were added to a solution of the crude product in N,N-dimethylformamide (6 ml), and the mixture was stirred at room temperature for 3 days. Water was added, and the mixture was extracted with ether and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=13/7) to give the desired compound (E)-2-benzylideneaminooxymethyl-α-methoxy-N-methylphenylacetamide (0.32 g, 51%) as white crystals.

1. extractionThe resulting mixture was extracted with ether
2. washwashed with saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. customEvaporation of the solvent
5. customgave a crude product (0.38 g) as an oil
6. stirringthe mixture was stirred at room temperature for 3 days
7. extractionthe mixture was extracted with ether
8. dry with materialdried over anhydrous magnesium sulfate
9. customThe solvent was evaporated
10. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=13/7)