Methyl iodide → N-(6-benzyloxy-3-methoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

Participants

Reaction Steps

0.5 g (1.3 mmol) of N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide (Example 1g) dissolved in 4 ml of DMF was added dropwise to a suspension of 0.05 g (1.7 mmol) of sodium hydride in 3 ml of DMF. The mixture was stirred at RT for 30 min, 0.25 g (1.8 mmol) of methyl iodide was added, and the mixture was stirred at RT for another 3 h. The reaction mixture was concentrated under reduced pressure, the residue was taken up in water and EA and the organic phase was washed with dilute hydrochloric acid and saturated sodium bicarbonate solution. Drying over magnesium sulfate and concentration under reduced pressure gave 0.52 g of N-(6-benzyloxy-3-methoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide, m.p. 119-121° C.

Provenance & Evidence