反应详情

温度

53 °C

To N-ethyl-p-toluenesulfonamide (5.01 g, 0.0251 mol) in DMF (50 mL) in a dry flask is added sodium hydride (80% in oil, 0.93 g, 0.031 mol). After gas evolution subsides, 1,3-dichloropropane (22.48 g, 0.199 mol) is added. The mixture is heated at 53° C. for 10 h then cooled and poured into ice water (300 mL), which is extracted twice with ether. The combined extracts are washed with 1% sodium bisulfite, water (3×), and brine. Removal of solvent by rotary evaporation then Kugelrohr distillation gives crude product, which is chromatographed on silica gel (30% hexane/CHCl3) to furnish 2.91 g product (42%) NMR (CDCl3) δ1.15 (t, 3H), 1.9-2.2 (m, 2H), 2.44 (s, 3H), 3.11-3.35 (m, 4H), 3.6 (t, 2H), 7.3 (d, 2H), 7.74 (d, 2H).

1. temperaturethen cooled
2. extractionis extracted twice with ether
3. washThe combined extracts are washed with 1% sodium bisulfite, water (3×), and brine
4. customRemoval of solvent
5. customby rotary evaporation
6. distillationKugelrohr distillation
7. customgives crude product, which
8. customis chromatographed on silica gel (30% hexane/CHCl3)