反应详情

To a stirred suspension of lithium aluminum hydride (1.928 g, 52.23 mmol) in THF (150 ml) at room temperature under nitrogen was added a suspension of 4-(heptyloxy)benzamide (6.146 g, 26.117 mmol). After refluxing for 22 h, reaction was cooled in an ice bath and quenched in the following order: water (2.09 ml), 15% NaOH (2.09 ml) and water (6.26 ml). The mixture was stirred for 3 h followed by the addition of Na2SO4. The mixture was filtered and concentrated in vac. The residue was taken up in Et2O, filtered, concentrated, and the resulting residue taken up in hexane, filtered, concentrated, and dried to give the desired product as a hazy yellow oil (4.872 g, 84%); 1H NMR (400 MHz, DMSO-d6) δ 0.86 (t, J=7 Hz, 3H), 1.22–1.42 (m, 8H), 1.64–1.72 (m, 2H), 1.82 (broad s, 2H), 3.13 (s, 2H), 3.89 (t, J=6.6 Hz, 2H), 6.80–6.84 (m, 2H), 7.17–7.21 (m, 2H); IR (film) 2940, 2850, 1510, 1250 cm−1; mass spectrum [(+)ESI], m/z 222 (M+H)+.

1. additionwas added
2. temperatureAfter refluxing for 22 h
3. customreaction
4. temperaturewas cooled in an ice bath
5. customquenched in the following order
6. additionfollowed by the addition of Na2SO4
7. filtrationThe mixture was filtered
8. concentrationconcentrated in vac
9. filtrationfiltered
10. concentrationconcentrated
11. filtrationfiltered
12. concentrationconcentrated
13. customdried