Реакция #1576121

Уравнение реакции

water

t-butyldimethylsilyl chloride

triethylamine

dehydroisoandrosterone

→

(3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-androst-5-en-17-one

Выход 90.3%

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter two days pour
2. 2
   ФильтрацияFilter the white solid
3. 3
   Промывкаwash with water (2×50 mL)
4. 4
   workup.DISSOLUTIONDissolve the solid in ethyl acetate (350 mL)
5. 5
   Промывкаwash with 0.5N hydrochloric acid (2×150 mL), half-saturated sodium bicarbonate (2×150 mL) and brine (100 mL)
6. 6
   СушкаDry the organic layer over anhydrous magnesium sulfate
7. 7
   Фильтрацияfilter
8. 8
   Концентрированиеconcentrate under vacuum
9. 9
   ДругоеPurify the residue by flash chromatography (ethyl acetate/hexane, 15:85, silica gel)

Методика

Dissolve dehydroisoandrosterone (10.0 g, 34.67 mmol) in dimethylformamide (DMF, 150 mL) under an atmosphere of nitrogen. Add t-butyldimethylsilyl chloride (5.23 g, 34.67 mmol), triethylamine (5.32 mL, 38.14 mmol) and a catalytic amount of 4-dimethylaminopyridine (0.21 g, 1.73 mmol) with stirring at room temperature. After two days pour the reaction into rapidly stirring water (1.5 L). Filter the white solid and wash with water (2×50 mL). Dissolve the solid in ethyl acetate (350 mL) and wash with 0.5N hydrochloric acid (2×150 mL), half-saturated sodium bicarbonate (2×150 mL) and brine (100 mL). Dry the organic layer over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (ethyl acetate/hexane, 15:85, silica gel) to provide (3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-androst-5-en-17-one (12.60 g) as a white solid, Rf =0.78 (ethyl acetate/hexane, 1:1, silica gel), mp 146°-148° C.

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