反应详情

To a suspension of 2′-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6′-(methoxycarbonylmethoxy)acetophenone (0.55 g) and 4-bromobenzaldehyde (0.19 g) in ethanol (9 mL) were added water (3 mL) and potassium hydroxide (0.67 g), and the mixture was stirred at room temperature for three days. To the reaction mixture was added 2 mol/L hydrochloric acid (7 mL), and the resulting mixture was extracted with ethyl acetate twice. The extracts were combined and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. To the residue were added sodium acetate (1.97 g), acetic acid (5 mL) and acetic anhydride (2.08 mL), and the mixture was stirred at 115° C. overnight. The reaction mixture was cooled to room temperature and poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1-3/2) to give the title compound (0.2 g).

1. extractionthe resulting mixture was extracted with ethyl acetate twice
2. dry with materialdried over anhydrous magnesium sulfate
3. customThe solvent was removed under reduced pressure
4. additionTo the residue were added sodium acetate (1.97 g), acetic acid (5 mL) and acetic anhydride (2.08 mL)
5. stirringthe mixture was stirred at 115° C. overnight
6. temperatureThe reaction mixture was cooled to room temperature
7. additionpoured into water
8. extractionthe resulting mixture was extracted with ethyl acetate
9. washThe extract was washed with water and brine
10. dry with materialdried over anhydrous sodium sulfate
11. customThe solvent was removed under reduced pressure
12. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1-3/2)