Hydroxyamine hydrochloride → (S)-1-(2,3-difluorophenyl)-2-((1,1,1-trifluorobut-3-en-2-yl)oxy)ethanone oxime

Participants

Reaction Conditions

Reaction Steps

(S)-1-(2,3-difluorophenyl)-2-((1,1,1-trifluorobut-3-en-2-yl)oxy)ethanone (3.91 g) was dissolved in anhydrous methanol (40 mL) and hydroxylamine hydrochloride (1.25 g) and sodium acetate (1.68 g) were added. The reaction mixture was heated to 50° C. for 90 min, then cooled to RT, concentrated in vacuo and the residue purified by silica gel chromatography (2% to 20% EtOAc in hexanes) to afford the title compound as a mixture of geometric isomers (4.10 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 4.04-4.26 (m 1H), 4.43-4.55 (m, 0.4H) 4.80-4.89 (m, 1.6H) 5.39-5.55 (m, 2H) 5.64-5.80 (m, 1H) 7.05-7.30 (m, 3H), 7.76 (br s, 0.2H), 8.30 (br s, 0.8H).

Provenance & Evidence