Oxygen → N-(3-Oxo-1-phenylpropyl)benzenesulfonamide

Participants

Reaction Steps

A stream of ozone was passed through a solution of the product of Step 3 (1.9 g, 6.6 mmol) in CH2Cl2 (90 mL) at −78° C. for 1 h. The solution was then purged with oxygen, Me2S (1.1 mL, 15 mmol) was added, the cooling bath removed and the mixture allowed to warm to RT. The reaction was complete after 3 days and the solvent removed under reduced pressure and the mixture purified by column chromatography on silica eluting 5–10% MeOH/CH2Cl2 to give the benzenesulfonamide as a colourless oil (1.6 g, 84%). 1H NMR (360 MHz, CDCl3) δ 2.90–3.10 (2H, m), 4.79–4.86 (1H, m), 5.45 (1H, d, J=7.4 Hz), 7.03–7.09 (2H, m), 7.13–7.18 (3H, m), 7.35–7.39 (2H, m), 7.46–7.51 (1H, m), 7.69–7.71 (2H, m), 9.64 (1H, s).

Provenance & Evidence