Dimethyl Sulfoxide → N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

Participants

Reaction Steps

4.25 g (39 mmol) of methyl-methanesulfonamide in 7.5 ml of DMSO were added dropwise to a suspension of 0.21 g (7 mmol) of 80 percent sodium hydride in 15 ml of DMSO, and the mixture was stirred at RT for 30 min. 8.2 g (29 mmol) of 6-benzyloxy-2,2-dimethyl-3,4-epoxychroman, dissolved in 18 ml of DMSO were then added dropwise, and the batch was heated at 50° C. for 2 days. The mixture was subsequently poured into water and the precipitate was filtered off with suction and dried well under reduced pressure, giving 8.8 g of N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide, m.p. 162-164° C.

Provenance & Evidence