Dimethyl Sulfoxide → 5-[Bis(methylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Participants

Reaction Steps

To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (60.0 g, 416 mmol) in DMSO (150 mL) was added carbon disulfide (25 mL, 420 mmol) and triethylamine (116 mL, 832 mmol). The mixture was stirred at room temperature for 1 h then cooled to 0° C. and 52 mL (830 mmol) of iodomethane was added. The reaction mixture was allowed to slowly warm to room temperature and stirred for 15h. The mixture was decanted into an ice—H2O mixture and a solid was precipitated by agitation of the solution. The solid was collected by filtration, washed with a 1:1 mixture of petroleum ether: Et2O, and dried under vacuum to provide 29.7 g (28.8%) of 5-(bis-methylsulfanyl-methylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione as an orange solid.

Provenance & Evidence