Sodium Acetate → HCID 86604004, compound

Participants

Reaction Steps

A solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (316 mg, 1.0 mmol), O-allylhydroxylamine hydrochloride (119 mg, 1.05 mmol) and anhydrous NaOAc (86 mg, 1.05 mmol) in EtOH (5 mL) was stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum and the residue filtered through a pad of silica (eluting with EtOAc/PE, 1:9). The residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:99 to 1:19) to afford N-[2-(1-allyloxyiminopropyl)-4-chlorophenyl]trifluoromethanesulfonamide 156 (116 mg, 31%), as a colorless oil. 1H n.m.r. (400 MHz, CDCl3) δ 11.57, br s, 1H; 7.67, d, J=8.8 Hz, 1H; 7.48, d, J=2.4 Hz, 1H; 7.33, dd, J=2.4 and 8.8 Hz, 1H; 6.00, m, 1H; 5.42, d, 3J=17.2 Hz, 1H; 5.36, d, 3J=10.4 Hz, 1H; 4.68, d, J=6.0 Hz, 2H; 2.83, q, J=7.6 Hz, 2H; 1.19, t, J=7.6 Hz, 3H. HRMS (M+) 370.0350.

Provenance & Evidence