反应详情

Part B. To a solution of lithium aluminum hydride (6.7 g, 0.176 mol) in dry tetrahydrofuran (300 mL), a solution of N-heptyl-5-hydroxypentanamide (19.0 g, 0.088 mol) in dry tetrahydrofuran (100 mL) under a nitrogen atmosphere was added dropwise. The reaction mixture was heated to reflux for 18 hours, allowed to cool to room temperature and was poured slowly into a stirred mixture of 10% aqueous sodium sulfate (400 mL) and ice (200 mL). The resulting slurry was filtered through a bed of Celite® and the filtrate was extracted with ethyl acetate (2×500 mL). The combined organic extracts were washed with water and brine, then dried over magnesium sulfate and concentrated to give a viscous yellow oil. The product was crystallized from hexane to give N-(5-hydroxypentyl)-N-heptylamine (15.2 g, 0.075 mol) as a white powder, mp 47°-48°. 1H NMR (CDCl3) δ3.63 (t,2H,J=8.4 Hz), 2.63 (quartet,4H,J=8.3 Hz), 2.39 (bs,2H), 1.66-1.24 (m,16H), 0.91 (t,3H,J=6.6 Hz).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 18 hours
3. filtrationThe resulting slurry was filtered through a bed of Celite®
4. extractionthe filtrate was extracted with ethyl acetate (2×500 mL)
5. washThe combined organic extracts were washed with water and brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated
8. customto give a viscous yellow oil
9. customThe product was crystallized from hexane