反应详情

To a solution of 4-methoxyphenylacetonitrile (E1) (1.002 g, 6.8 mmol) and 1,5-dibromopentane (1.886 g, 8.2 mmol) in dry dimethylformamide (15 ml) at ice bath temperature slowly (ca. 2-3 minutes) a 60% suspension of NaH in mineral oil (0.579 g, 14.4 mmol) was added. The obtained reaction mixture was stirred for 15 minutes at ice bath temperature and for 1.5 hours at room temperature, then the contents were poured into benzene (75 ml). The mixture was successively washed with water (3×75 ml), brine (25 ml), and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silicagel (50 g) with petroleum ether-ethyl acetate (5:1) as eluent to give the title compound (0.924 g, 63%) as a white solid. 1H NMR (CDCl3, HMDSO) δ: 1.00-2.28 (10H, m); 3.81 (3H, s); 6.90 (2H, d, J=9.0 Hz); 7.40 (2H, d, J=9.0 Hz).

1. customThe obtained reaction mixture
2. waitfor 1.5 hours at room temperature
3. washThe mixture was successively washed with water (3×75 ml), brine (25 ml)
4. dry with materialdried (Na2SO4)
5. customThe solvent was evaporated
6. customthe residue was chromatographed on silicagel (50 g) with petroleum ether-ethyl acetate (5:1) as eluent