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

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.

1. temperaturethen cooled to 0° C.
2. temperatureto slowly warm to room temperature
3. stirringstirred for 15h
4. customThe mixture was decanted into an ice—H2O mixture
5. customa solid was precipitated by agitation of the solution
6. filtrationThe solid was collected by filtration
7. washwashed with a 1:1 mixture of petroleum ether
8. dry with materialEt2O, and dried under vacuum

ORDレコード

ord-7605cbd5c42040898eafe0a24eca1a61

出典データセット

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07119102B2