Dimethyl Sulfoxide → HCID 52916043, compound

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (34.15 g, 247 mmol) was slowly added to a solution of diethyl 1,3-acetone dicarboxylate (50 g, 247 mmol) in anhydrous DMSO (64 mL) at room temperature The reaction mixture was stirred for 30 minutes and was cooled to 5° C. Carbon disulfide (14.92 mL, 247 mmol) was added dropwise over 30 minutes at 5-10° C., followed by stirring at 0° C. for 1 h. Methyl iodide (30.8 mL, 494 mmol) was then added dropwise at 10° C. and the reaction mixture was stirred at this temperature for 1 h. After quenching the reaction with water, it was extracted with DCM. The combined organics extracts were dried (MgSO4) and concentrated under reduced pressure. Purification by silica gel (1:7 EtOAc/hexanes) gave 20.2 g (26%) of the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 4.18 (q, 2H), 4.08 (q, 2H), 3.71 (s, 2H), 2.45 (s, 6H), 1.23 (t, 3H), 1.18 (t, 3H). MS (ES) [m+H] calc'd for C11H8F4O3, 307; found 307.

Provenance & Evidence