反应 #586166

反应方程式

ethyl acetate

51

2-[(5-methyl-1H-indol-1-yl)methyl]pent-4-enenitrile

LiAlH4

→

52

收率 39.0%

2-[(5-methylindolyl)methyl]pent-4-enylamine

收率 39.0%

溶剂

THF

反应条件

后处理

1. 1
   温度cooled to −78° C.
2. 2
   其他The reaction was quenched by the addition of moister Na2SO4
3. 3
   过滤filtered through celite
4. 4
   洗涤washed with EtOAc (3×100 mL) and MeOH (3×150 mL)
5. 5
   其他Evaporation
6. 6
   其他provided a residue, which
7. 7
   其他was purified by silica gel flash chromatography

实验过程

To a stirred solution of 51 (8.82 g, 39.3 mmol) in THF (400 mL) at 0° C. was added LiAlH4 (4.77 g, 118 mmol). The mixture was stirred at room temperature overnight, then cooled to −78° C. and ethyl acetate (60 mL) was added followed by 10% NaOHaq (15 mL). The reaction was quenched by the addition of moister Na2SO4, filtered through celite, washed with EtOAc (3×100 mL) and MeOH (3×150 mL). Evaporation provided a residue, which was purified by silica gel flash chromatography to provide 52 as colorless oil. (3.52 g, 39% yield). H NMR (d6-DMSO) δ 7.34-7.27 (m, 3H), 6.93 (d, 1H, J=1.5 Hz & 8.3 Hz), 6.31 (d, 1H, J=3.0 Hz), 5.78 (m, 1H), 5.06-4.99 (m, 2H), 4.16 (dd, 1H, J=7.0 Hz & 14.2 Hz), 4.00 (dd, 1H, J=6.5 Hz & 14.2 Hz), 2.42 (t, 2H, J=4.5 Hz), 2.36 (s, 3H), 2.05 (m, 1 H), 1.98-1.90 (m, 2H). FABMS (+Ve) m/z 229 [MH+].

来源