反応 #81134

反応方程式

sodium hydrogencarbonate

tert-butyldimethylchlorosilane

imidazole

(1RS, 2SR)-2-(4-bromophenyl)-3-(4-chlorophenyl)-1-methylpropanol

→

(2RS, 3SR)-3-(4-bromophenyl)-2-(tert-butyldimethylsilyloxy)-4-(4-chlorophenyl)butane

収率 75.0%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   抽出extracted by an addition of ethyl ether
2. 2
   洗浄Then, the organic layer was washed with a saturated sodium chloride aqueous solution
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   その他The drying agent was separated by filtration
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

実験手順

0.70 g of (1RS, 2SR)-2-(4-bromophenyl)-3-(4-chlorophenyl)-1-methylpropanol was dissolved in 7 ml of dimethylformamide, and 0.34 g of tert-butyldimethylchlorosilane and 0.18 g of imidazole were added thereto. The mixture was stirred at room temperature overnight. The reaction solution was poured into a saturated sodium hydrogencarbonate aqueous solution and extracted by an addition of ethyl ether. Then, the organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane) to obtain 0.70 g (yield: 75%) of [(2RS, 3SR)-3-(4-bromophenyl)-2-(tert-butyldimethylsilyloxy)-4-(4-chlorophenyl)butane as colorless oily substance.

出典