Hydrogen Peroxide → N-(2-(3-Chlorophenyl)-5-hydroxypentyl)-N-methylbenzenesulfonamide

Participants

Reaction Steps

9-BBN (119 mg, 0.488 mmol) was added in one portion to an ice cold solution of N-(2-(3-chlorophenyl)pent-4-enyl)-N-methylbenzenesulfonamide (100 mg, 0.286 mmol) in 1.0 mL of THF, and the mixture was allowed to warm to room temperature. After 15 h, an additional portion of 9-BBN (26 mg, 0.11 mmol) was added and stirring was continued for another 1 h. Aqueous 2.5 N sodium hydroxide solution (0.29 mL, 0.73 mmol) and aqueous 30% hydrogen peroxide solution (0.176 mL) were added and the mixture was stirred 45 min at room temperature, 5 h at 50 ° C., and overnight at room temperature. The reaction was concentrated and the residue was partitioned between 25 mL of ethyl acetate and a mixture of 20 mL of water and 5 mL of brine. The aqueous layer was extracted with 2×25 mL of ethyl acetate. The combined organic layers were washed with 25 mL of brine, dried over sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel, eluting with 5-50% ethyl acetate in dichloromethane to give 39 mg the title compound. 1NMR (400 MHz, CD3OD): δ 7.72 (d, 2H, J=8 Hz), 7.63 (tt, 11H, J=8, 1 Hz), 7.56 (t, 2H, J=8 Hz), 7.29 (dd, 1H, J=9, 8 Hz), 7.24-7.20 (m, 2H), 7.16 (dt, 1H, J=8, 1 Hz), 3.49 (t, 2H, J=7 Hz), 3.24 (dd, 1H, J=13, 8 Hz), 3.13 (dd, 1H, J=13, 7 Hz), 2.97-2.88 (m, 1H), 2.59 (s, 3H), 1.87-1.77 (m, 1H), 1.65-1.54 (m, 1H), 1.45-1.27 (m, 2H). Mass spectrum (NH3 /CI): m/z=368 (M+1).

Provenance & Evidence