反応 #1973908

反応方程式

hydrogen

lithium

hydride

2-Benzyloxy-N-(2-chloro-5-methoxy-phenyl) acetamide

lithium aluminium hydride

→

(2-Benzyloxy-ethyl)-(2-chloro-5-methoxyphenyl) amine

収率 101.7%

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度The reaction was then heated
3. 3
   温度to reflux for 4 h
4. 4
   その他to stand at RT over the weekend
5. 5
   その他The reaction was then quenched by the dropwise addition of water (50 mL) to the stirred solution
6. 6
   温度to reflux
7. 7
   濃縮The reaction was then concentrated in vacuum to a slurry
8. 8
   workup.ADDITIONWater (200 mL) and ethyl acetate (200 mL) were added
9. 9
   ろ過The reaction was then filtered through celite
10. 10
    その他to remove the precipitated aluminium hydroxide
11. 11
    その他the ethyl acetate solution was separated
12. 12
    乾燥dried over magnesium sulfate
13. 13
    濃縮concentrated in vacuo

実験手順

2-Benzyloxy-N-(2-chloro-5-methoxy-phenyl) acetamide (2) (18.9 g, 62.0 mmol) in THF (100 mL) was stirred and lithium aluminuim hydride (4.9 g, 130.0 mmol) was added slowly over 15 min. There was a rapid evolution of hydrogen gas as the first of the lithium aluminium hydride was added. The reaction was then heated to reflux for 4 h and allowed to stand at RT over the weekend. The reaction was then quenched by the dropwise addition of water (50 mL) to the stirred solution. There was a violent evolution of hydrogen causing the reaction mixture to reflux. The reaction was then concentrated in vacuum to a slurry. Water (200 mL) and ethyl acetate (200 mL) were added and the mixture vigorously shaken. The reaction was then filtered through celite to remove the precipitated aluminium hydroxide and the ethyl acetate solution was separated, dried over magnesium sulfate and concentrated in vacuo to afford 18.4 g (quantitative) of (2-Benzyloxy-ethyl)-(2-chloro-5-methoxyphenyl) amine (3) as a gum. The structure was confirmed by 13C NMR (75 MHz, CDCl3) δC 43.3, 55.3, 68.2, 73.0, 98.1, 101.8, 111.6, 127.6, 127.7, 128.4, 129.3, 137.9, 144.8, and 159.5.

出典