反応 #48617

反応方程式

sodium chloride

[(R)-1-(tert-butyl-dimethylsilanyloxymethyl)-2-hydroxyethyl]-carbamic acid tert-butyl ester

ethyl vinyl ether

acetonitrile

N-iodosuccinimide

→

desired compound

収率 34.0%

[(R)-2-(tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester

収率 34.0%

反応条件

後処理

1. 1
   抽出Extract with ethyl acetate
2. 2
   洗浄wash with water and saturated aqueous sodium chloride
3. 3
   乾燥dry (magnesium sulfate)
4. 4
   ろ過filter
5. 5
   濃縮concentrate
6. 6
   その他Purify
7. 7
   洗浄(silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate)

実験手順

Dissolve [(R)-1-(tert-butyl-dimethylsilanyloxymethyl)-2-hydroxyethyl]-carbamic acid tert-butyl ester (1.0 g, 3.27 mmol) and ethyl vinyl ether (0.20 g, 2.73 mmol) in acetonitrile (20 mL) and add N-iodosuccinimide (0.735 g, 3.27 mmol). Stir at room temperature 72 hours and pour into saturated aqueous sodium chloride. Extract with ethyl acetate, wash with water and saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify (silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate) to give the desired compound (462 mg, 34%).

出典