Reaktion #81134

Reaktionsgleichung

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

Ausbeute 75.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted by an addition of ethyl ether
2. 2
   WaschenThen, the organic layer was washed with a saturated sodium chloride aqueous solution
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   SonstigeThe drying agent was separated by filtration
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Vorschrift

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.

Quelle