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

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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 1 H), 4.43-4.55 (m, 0.4 H) 4.80-4.89 (m, 1.6 H) 5.39-5.55 (m, 2 H) 5.64-5.80 (m, 1 H) 7.05-7.30 (m, 3 H), 7.76 (br s, 0.2 H), 8.30 (br s, 0.8 H).

Provenance & Evidence