Iodoethane → N-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-N-ethylmethanesulfonamide

Participants

Reaction Steps

7.2 g (20 mmol) of 6-benzyloxy-4-(methylsulfonyl)amino-2,2-dimethylchroman were introduced in portions at 10° C. into a suspension of 0.82 g (27 mmol) of sodium hydride (80 per cent dispersion) in 60 ml of DMA. After stirring at RT for 2 h, 2.2 ml (26.5 mmol) of ethyl iodide were added dropwise, the temperature rising to 32° C. The mixture was then heated to 35-40° C. for 2 h, concentrated in vac., treated with water, the resinous product was taken up EA, the solution was dried and concentrated and the residue was chromatographed using n-heptane/EA (2:1) on silica gel. 6 g of product were crystallized from appropriate fractions using petroleum ether/diisopropyl ether (1:1), m.p. 104-106° C.

Provenance & Evidence