Реакция #1330397

Уравнение реакции

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

Imidazole

tert-butyldiphenylsilyl chloride

→

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

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   workup.DISSOLUTIONWhen all had dissolved
2. 2
   Промывкаwashed with water (2×) and brine
3. 3
   Сушкаdried over anhydrous sodium sulfate
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеPurification by flash chromatography (Biotage 40M, 5:95 ethyl acetate-hexanes)

Методика

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%).

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