Sodium hydride → HCID 86754520, compound

Participants

Reaction Steps

Methyl [(6-chloro-3-hydroxy-2,2-dimethylchroman-4-yl)methanesulfonylamino]acetate A solution of 3.0 g (10 mmol) of N-(6-chloro-3-hydroxy-2,2-dimethylchroman-4-yl)methanesulfonamide was added dropwise to a solution of 0.33 g (11.3 mmol) of 80 percent sodium hydride in 25 ml of DMF and the mixture was additionally stirred at RT for 1 h. 1.53 g (10 mmol) of methyl bromoacetate were then added, the mixture was stirred overnight at RT and then the solvent was stripped off in vacuo. The residue was taken up in EA and water, the organic phase was concentrated and the product was purified by chromatography on silica gel using cyclohexane/ethyl acetate 9:1. 2.0 g of methyl [(6-chloro-3-hydroxy-2,2-dimethylchroman-4-yl)-methanesulfonylamino]acetate were obtained; m.p. 148-150° C.

Provenance & Evidence