Oxygen → HCID 89180724, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 91A (170 mg, 0.353 mmol), DCM (5.0 mL), and MeOH (5.0 mL) was cooled to 78° C. and perfused with oxygen gas for 3 min. Then using an ozonator, a stream of O3 in oxygen gas was bubbled through the solution for 5 min. After this, the reaction was stirred for 10 min, then sparged with oxygen gas for 2 min to drive out unreacted ozone in solution. While the reaction was still at 78° C., dimethylsulfide (200 μL) was added and the reaction allowed to warm to 0° C. After 30 min, 10% w/v aq Na2S2O3 (5 mL) was added and the reaction was warmed to 23° C. and stirred for 10 min. The reaction was diluted with H2O (20 mL) and extracted with DCM (3×15 mL). Combined organic layers were dried (Na2SO4), filtered, and concentrated. More DCM was added and the reaction was concentrated once more to remove residual methanol, giving 91B (165 mg, 97% yield). 1H-NMR: 400 MHz, (CDCl3) δ: 10.04 (s, 1H), 8.00 (s, 1H), 5.60 (s, 1H), 4.22-4.00 (m, 2H), 2.51 (s, 3H), 1.16 (s, 9H), 1.14 (t, J=6.8 Hz, 3H). 19F-NMR: 376 MHz, (CDCl3) δ: −73.6.

Provenance & Evidence