反应详情

A solution of anthraldehyde (9.595 g, 0.0465 mol) and 5-amino-1-pentanol (15.00 g, 0.116 mol) dissolved in 500 mL ethanol at 0° C. was stirred for 3 h. After warming to room temperature the solvent was removed under reduced pressure, and 150 mL of ethanol containing NaBH4 (4.65 g, 0.1229 mol) was added slowly with stirring. The resulting mixture was allowed to stir overnight. The ethanol was removed under reduced pressure and to the brown oil/solid mixture was added 150 mL diethyl ether. Water was added dropwise to this solution until the evolution of hydrogen ceased, followed by the addition of 500 mL water. The ether phase was isolated, washed with 2×50 mL water, dried over sodium sulfate and filtered on a sintered-glass frit. Removal of the solvent afforded 12.17 g (89.2% yield) of 5 as a golden solid; 1H NMR (300.13 MHz, CD3CN) δ 1.51 (m, 6H), 2.81 (t, 2H), 3,49 (t, 2H), 4.68 (s, 2H), 7.52 (m, 4H), 8.05 (d, 2H), 8.44 (m, 3H); 13C—{1H} NMR (75.4 MHz, CDCl3) δ 133.1, 132.0, 131.7, 130.4, 128.6, 127.4, 126.2, 125.1, 62.9, 51.1, 45.8, 33.5, 30.3, 24.8.

1. customwas removed under reduced pressure, and 150 mL of ethanol
2. additionwas added slowly
3. stirringwith stirring
4. stirringto stir overnight
5. customThe ethanol was removed under reduced pressure and to the brown oil/solid mixture
6. additionwas added 150 mL diethyl ether
7. additionWater was added dropwise to this solution until the evolution of hydrogen
8. additionfollowed by the addition of 500 mL water
9. customThe ether phase was isolated
10. washwashed with 2×50 mL water
11. dry with materialdried over sodium sulfate
12. filtrationfiltered on a sintered-glass frit
13. customRemoval of the solvent