Реакция #70403

Уравнение реакции

3β-tert-butyldimethylsilyloxyandrostane-6α,17β-diol

→

3β-tert-butyldimethylsilyloxyandrostane-6,17-dione

Выход 75.0%

Растворители

DMSO

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   ДругоеAfter 1.5 h the mixture was quenched at room temperature by addition of H2O (300 mL)
3. 3
   ФильтрацияAfter 15 min the mixture was filtered
4. 4
   Промывкаthe cake was washed with H2O
5. 5
   ЭкстракцияThe cake was extracted with Et2O (4×)
6. 6
   СушкаThe combined organic extracts were dried over Na2SO4
7. 7
   Другоеevaporated to dryness

Методика

To a stirred suspension of 3β-tert-butyldimethylsilyloxyandrostane-6α,17β-diol (EP 0825197 A2, 6.21 g) in DMSO (160 mL), IBX (16.45 g) was added at room temperature. After 1.5 h the mixture was quenched at room temperature by addition of H2O (300 mL). After 15 min the mixture was filtered and the cake was washed with H2O. The cake was extracted with Et2O (4×). The combined organic extracts were dried over Na2SO4 and evaporated to dryness to give 3β-tert-butyldimethylsilyloxyandrostane-6,17-dione (0.36 g, 75%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 3.54 (1H, m), 2.47-1.08 (20H, m), 0.84 (9H, s), 0.77 (3H, s), 0.66 (1H, s), 0.01 (6H, s).

Источник