Acetone → HCID 57595178, compound

Participants

Reaction Steps

A 100 mL round bottom flask containing sulfide 42 (720 mg, 1.70 mmol) was charged with methanol (20 mL), then a solution of Oxone (3.14 g, 5.10 mmol) in water (20 mL), then acetone (20 mL). After stirring at room temperature for 12 hours, the reaction was cooled to below −20° C. in a dry ice/isopropanol bath, then SO2 was bubbled in for 5 minutes. The reaction was then concentrated under reduced pressure to remove organic solvent, and the resulting aqueous mixture was neutralized with an aqueous potassium carbonate solution. The resulting aqueous solution was extracted exhaustively into ethyl acetate, and the organic fractions were pooled, dried over MgSO4, filtered, and concentrated under reduced pressure, and the sulfone product was not purified further. Yield of 43: 470 mg (61%). 1H NMR (400 MHz, DMSO-d6) δ 2.30 (s, 6H), 2.49 (m, 2H), 3.47 (s, 3H), 4.85 (m, 1H), 5.60 (m, 1H), 7.25 (d, J=7.4 Hz, 1H), 7.33 (t, J=8.8 Hz, 2H), 7.37 (d, J=5.6 Hz, 1H), 7.71 (m, 3H), 8.80 (d, J=5.6 Hz, 1H), 9.51 (d, J=7.4 Hz, 1H). MS (ESI+) 456.2.

Provenance & Evidence