Reacción #1118678

Ecuación de reacción

LiAlH4

methyl 1-methylindole-3-acetate

→

product

3-(2-Hydroxyethyl)-1-methylindole

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was refluxed for 1 h
2. 2
   Otroquenched by the sequential addition of 2 mL of H2O, 2 mL of 15% aqueous NaOH and finally 6 mL of H2O
3. 3
   FiltraciónThe resulting slurry was filtered
4. 4
   Lavadothe filter cake was washed with additional tetrahydrofuran
5. 5
   OtroEvaporation of the filtrate

Procedimiento

To a suspension of LiAlH4 (2.0 g, 0.052 mol) in 50 mL of dry tetrahydrofuran was added dropwise a solution of methyl 1-methylindole-3-acetate (5.25 g, 0.026 mol) in 70 mL of dry tetrahyqrofuran at -10° C. under Ar. The mixture was refluxed for 1 h and then it was cooled at 0° C. and quenched by the sequential addition of 2 mL of H2O, 2 mL of 15% aqueous NaOH and finally 6 mL of H2O. The resulting slurry was filtered and the filter cake was washed with additional tetrahydrofuran. Evaporation of the filtrate gave the product (40 g, 89%) as an oil which was used without further purification.

Fuente