反応 #1868

反応方程式

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

収率 96.1%

溶媒

acetic acid

反応条件

後処理

1. 1
   温度cooling
2. 2
   抽出followed by extraction with ethyl acetate (200 ml×2)
3. 3
   洗浄The ethyl acetate layer was washed with 1N sodium hydroxide, which
4. 4
   乾燥was dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONby distilling off the solvent under reduced pressure
6. 6
   その他The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1)

実験手順

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.

出典