反应详情

To a stirred solution of N-(5-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (9-01) (1.7 g, 5.46 mmol) in methanol (30 mL) aqueous NaOH (218.4 mg, 5.46 mmol, 2M) was added. After heating to reflux, benzyl bromide (0.654 mL, 5.46 mmol) was added and heating was continued for 24 h. After completion of the reaction, the mixture was concentrated to remove methanol, then diluted with water and extracted with dichloromethane. The combined organic layer was washed with saturated NaHCO3 solution, water and brine, dried over Na2SO4 and concentrated under reduced pressure. It was then purified using normal column chromatography to get N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (10-01) (1.02 gm, 46.48%) as a white solid.

1. temperatureAfter heating
2. temperatureto reflux
3. temperatureheating
4. customAfter completion of the reaction
5. concentrationthe mixture was concentrated
6. customto remove methanol
7. additiondiluted with water
8. extractionextracted with dichloromethane
9. washThe combined organic layer was washed with saturated NaHCO3 solution, water and brine
10. dry with materialdried over Na2SO4
11. concentrationconcentrated under reduced pressure
12. customIt was then purified