Reacción #53437

Ecuación de reacción

NaOH

ethyl indole-2-carboxylate

lithium aluminum hydride

water

water

→

1H-indol-2-ylmethanol

Rendimiento 83.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   SecadoThe resulting suspension is dried (Na2SO4)
2. 2
   Filtraciónfiltered through celite
3. 3
   ConcentraciónAfter concentration under reduced pressure
4. 4
   Otrothe white solid (34.0 g) is crystallized from EtOAc/hexanes

Procedimiento

To a suspension of lithium aluminum hydride (10.6 g, 264 mmol) in THF (200 mL) is added dropwise a solution of ethyl indole-2-carboxylate (50.0 g, 256 mmol) in THF (250 mL) over 25 minutes. After 3 h, water (10.6 mL) is carefully added, followed by 15% NaOH (10.6 mL), followed by additional portion of water (31.8 mL). The resulting suspension is dried (Na2SO4) and filtered through celite. After concentration under reduced pressure, the white solid (34.0 g) is crystallized from EtOAc/hexanes to give white needles for 1H-indol-2-ylmethanol. Yield 83%. HRMS (FAB) calcd for C9H9NO+H 148.0762, found 148.0771.

Fuente