Reacción #1868

Ecuación de reacción

water

2-amino-5-chloro-α-(2-chloro phenyl)benzyl alcohol

2,4-dimethoxy benzaldehyde

sodium borohydride

→

5-chloro-α-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol

Rendimiento 96.1%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Extracciónfollowed by extraction with ethyl acetate (200 ml×2)
3. 3
   LavadoThe ethyl acetate layer was washed with 1N sodium hydroxide, which
4. 4
   Secadowas dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONby distilling off the solvent under reduced pressure
6. 6
   OtroThe residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1)

Procedimiento

To a solution of 2-amino-5-chloro-α-(2-chloro phenyl)benzyl alcohol (5.0 g) and 2,4-dimethoxy benzaldehyde (3.72 g) in acetic acid (50 ml) was added, under ice-cooling, sodium borohydride (0.94 g). The mixture was stirred for one hour at room temperature, which was poured into water (200 ml), followed by extraction with ethyl acetate (200 ml×2). The ethyl acetate layer was washed with 1N sodium hydroxide, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1) to give 5-chloro-α-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol (7.5 g) as an oily product.

Fuente