反应详情

In 70 mL of methanol was dissolved 16.4 g of the aforesaid 2-bromo-1-[2-hydroxy-5-(2-hydroxyethyl)-4-methoxyphenyl]-1-ethanone, and 17.3 g of sodium acetate was added to the solution, after which the resulting mixture was heated under reflux for 5 minutes. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was dissolved in 150 mL of methanol and to the resulting solution was added 6.30 g of sodium borohydride in small portions, after which the resulting mixture was stirred at room temperature for 1 hour. Then, the resulting solution was adjusted to pH 1 with 6 mol/L hydrochloric acid and stirred at room temperature for another 1 hour. The reaction mixture was concentrated under reduced pressure and water and ethyl acetate were added thereto, after which the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 1.48 g of 2-(6-methoxy-1-benzofuran-5-yl)-1-ethanol as light-yellow crystals.

1. additionwas added to the solution
2. temperatureafter which the resulting mixture was heated
3. temperatureunder reflux for 5 minutes
4. temperatureAfter the reaction mixture was cooled
5. customthe organic layer was separated
6. washThe organic layer was washed with water
7. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
8. distillationdistilled under reduced pressure
9. customto remove the solvent
10. dissolutionThe residue was dissolved in 150 mL of methanol and to the resulting solution
11. additionwas added 6.30 g of sodium borohydride in small portions
12. stirringstirred at room temperature for another 1 hour
13. concentrationThe reaction mixture was concentrated under reduced pressure and water and ethyl acetate
14. additionwere added
15. customafter which the organic layer was separated
16. washThe organic layer was washed with water
17. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
18. distillationdistilled under reduced pressure
19. customto remove the solvent
20. customThe residue was purified by a column chromatography (eluent; hexane:ethyl acetate=4:1)