Reaktion #1330397

Reaktionsgleichung

Methyl (S)-(+)-3-hydroxybutyrate

Imidazole

tert-butyldiphenylsilyl chloride

→

(S)-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONWhen all had dissolved
2. 2
   Waschenwashed with water (2×) and brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification by flash chromatography (Biotage 40M, 5:95 ethyl acetate-hexanes)

Vorschrift

Methyl (S)-(+)-3-hydroxybutyrate (0.48 g, 4.04 mmol) (Aldrich) was dissolved in dichloromethane (6 mL, dried over molecular sieves). Imidazole (0.39 g, 5.65 mmol) (Aldrich) was added. When all had dissolved, tert-butyldiphenylsilyl chloride (1.05 mL, 4.04 mmol) was added dropwise and the mixture was stirred at room temperature for 4.5 hours. The reaction mixture was diluted with additional dichloromethane, washed with water (2×) and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by flash chromatography (Biotage 40M, 5:95 ethyl acetate-hexanes) gave (S)-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester. (Yield 1.33 g, 92.4%).

Quelle