Reacción #1973908

Ecuación de reacción

hydrogen

lithium

hydride

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

lithium aluminium hydride

→

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

Rendimiento 101.7%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturaThe reaction was then heated
3. 3
   Temperaturato reflux for 4 h
4. 4
   Otroto stand at RT over the weekend
5. 5
   OtroThe reaction was then quenched by the dropwise addition of water (50 mL) to the stirred solution
6. 6
   Temperaturato reflux
7. 7
   ConcentraciónThe reaction was then concentrated in vacuum to a slurry
8. 8
   workup.ADDITIONWater (200 mL) and ethyl acetate (200 mL) were added
9. 9
   FiltraciónThe reaction was then filtered through celite
10. 10
    Otroto remove the precipitated aluminium hydroxide
11. 11
    Otrothe ethyl acetate solution was separated
12. 12
    Secadodried over magnesium sulfate
13. 13
    Concentraciónconcentrated in vacuo

Procedimiento

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.

Fuente