Oxygen → HCID 57987432, compound

Participants

Reaction Conditions

Reaction Steps

Dimethyl allyl{2-oxo-2-[4-(trifluoromethyl)phenyl]ethyl}malonate (20 g, 0.055 mol) was dissolved in DCM (180 ml) and the solution was cooled to −78° C. Oxygen, containing ozone, was bubbled through the solution until a blue coloration persisted. The mixture was then purged with nitrogen for 10 min in then dimethyl sulfide (20 ml, 0.275 mol) was added and the mixture was stirred overnight at room temperature. Water (500 ml) was added and the mixture was extracted with DCM. The organic layer was separated and was washed with brine, then dried (MgSO4) and concentrated in vacuo to give the product as an oil. This was purified by chromatography on silica using hexane/EtOAc (9:1 to 1:1) as eluant to afford the product (4 g). 1H NMR (500 MHz, CDCl3): δ 3.46 (2H, s), 3.77 (7H, s), 3.93 (2H, s), 7.74 (2H, d, J 8.2), 8.06 (2H, d, J 8.1), 9.73 (1H, s).

Provenance & Evidence