Carbon Tetrachloride → HCID 59451471, compound

Participants

Reaction Steps

A solution of N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}acetamide (1.64 g, 7.5 mmol), triphenylphosphine (4.9 g, 18.8 mmol), and carbon tetrachloride (1.8 mL, 18.8 mmol) in acetonitrile (75 mL) was heated at 45° C. for 6 h. The reaction was concentrated and the residue was stirred in CH2Cl2 (80 mL) and 0.5 N NaOH (70 mL) for 15 min. The organic layer was isolated, dried (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash column chromatography (5-70% EtOAc:hexanes) to give the title compound as a yellow solid, in assumed quantitative yield due to inseparable triphenylphosphine oxide. 1H NMR (400 MHz, CDCl3) δ ppm 7.28-7.37 (m, 5H), 4.50 (s, 2H), 4.48 (s, 2H), 2.37 (s, 3H).

Provenance & Evidence