Sodium hydride → N-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-N-(2-methoxyethyl)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

8.9 g (25 mmol) of 6-benzyloxy-4-(methylsulfonyl)amino-2,2-dimethylchroman (Example 1e) were introduced in portions at 10° C. into a suspension of 0.54 g (30 mmol) of sodium hydride (60% dispersion) in 80 ml of DMA. After stirring at 50° C. for 30 min, 2.2 ml (22 mmol) of 2-methoxyethyl bromide were added dropwise at RT. The mixture was then heated to 110° C. for 1 h, concentrated in vac., the residue was treated with water and aqueous hydrochloric acid, the resinous product was taken up with EA, the solution was dried and concentrated, and the residue was chromatographed on silica gel using toluene/EA (3:1). 2.2 g of product were crystallized from appropriate fractions using petroleum ether, m.p. 66-68° C.

Provenance & Evidence