Water → HCID 59570926, compound

Participants

Reaction Steps

To a solution of methyl [(2S,3S)-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-8-yl]methanesulfonate (58.6 g) in acetone (800 mL) was added sodium iodide (52.3 g) at room temperature. The mixture was heated under reflux overnight and again cooled to room temperature. To the reaction mixture were added water and ethyl acetate. The organic layer was separated, sequentially washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous magnesium sulfate. The crude product obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=1:0-50:1-30:1-10:1) to obtain (2S,3S)-8-(iodomethyl)-2,3-diphenyl-1,4-dioxaspiro[4.5]decane (40.6 g) as a pale yellow oily substance.

Provenance & Evidence