Pyridine → N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

Participants

Reaction Steps

To a stirred solution of 2-aminomethyl-5-benzyloxy-pyran-4-one (5) (4.4 gm, 19.05 mmol) in dichloromethane (100 mL) was added pyridine (6.15 mL, 76.19 mmol) under ice cold conditions, followed by addition of benzene sulfonyl chloride (6-01) (6.07 mL, 47.62 mmol) and the reaction mixture was stirred at room temperature for 16 h. After completion of the reaction, it was quenched with water and extracted with ethyl acetate. The combined organic layer was washed with saturated NaHCO3, water and brine, dried over Na2SO4 and concentrated under reduced pressure. It was then purified using normal column chromatography to get N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (7-01) (2.3 gm, 32.51%) as an off white solid.

Provenance & Evidence