反应详情

A solution of N-{1-cyano-2-[(phenylmethyl)oxy]ethyl}butanamide (1.60 g, 6.5 mmol), triphenylphosphine (4.3 g, 16.3 mmol), and carbon tetrachloride (1.6 mL, 16.3 mmol) in acetonitrile (65 mL) was heated at 42° C. for 12 h. The reaction was then concentrated and the residue was stirred in CH2Cl2 (70 mL) and 0.5 N NaOH (60 mL) for 15 min. The organic layer was isolated, dried (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash column chromatography (5-40% EtOAc:hexanes) to give the title compound as a light yellow solid, in assumed quantitative yield due to inseparable triphenylphosphine oxide. 1H NMR (400 MHz, CDCl3) δ 7.30-7.40 (m, 5H), 4.52 (s, 4H), 2.58-2.68 (m, 2H), 1.68-1.82 (m, 2H), 0.97 (t, 3H).

1. concentrationThe reaction was then concentrated
2. customThe organic layer was isolated
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customthe residue was purified by silica gel flash column chromatography (5-40% EtOAc:hexanes)