반응 #70380

반응 방정식

3β-hydroxy-5α,6α-epoxyandrostane-17-one

3β-hydroxy-5β,6β-epoxyandrostan-17-one

i-PrOH

→

5α-hydroxyandrostane-3,6,17-trione

수율 75.0%

용매

acetone

Jones reagent

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   온도maintaining the temperature below 40° C
3. 3
   workup.ADDITIONwas added and, after further 10 min
4. 4
   여과the suspension was filtered
5. 5
   기타the filtrate evaporated to dryness
6. 6
   workup.ADDITIONThe residue was treated with H2O (300 mL)
7. 7
   추출extracted with EtOAc (3×100 mL)
8. 8
   세척The combined organic extracts were washed with H2O (100 mL), 5% aqueous NaHCO3 solution (100 mL), H2O (100 mL)
9. 9
   건조dried over Na2SO4
10. 10
    기타evaporated to dryness

실험 절차

To a solution of a 1/1 mixture of 3β-hydroxy-5α,6α-epoxyandrostane-17-one and 3β-hydroxy-5β,6β-epoxyandrostan-17-one (2.10 g, 6.90 mmol) in acetone (38 mL), Jones reagent (8.35 mL) was added dropwise, maintaining the temperature below 40° C. 5 min after completion of the addition, i-PrOH (10 mL) was added and, after further 10 min, the suspension was filtered and the filtrate evaporated to dryness. The residue was treated with H2O (300 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with H2O (100 mL), 5% aqueous NaHCO3 solution (100 mL), H2O (100 mL), dried over Na2SO4 and evaporated to dryness to give 5α-hydroxyandrostane-3,6,17-trione as a white solid (1.65 g, 75%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 5.00 (1H, s), 2.85 (2H, m), 2.45-1.25 (17H, m), 1.06 (3H, s), 0.88 (3H, s).

출처