반응 #430487

반응 방정식

3,17β-dihydroxyestra-1,3,5(10)-triene-4-carboxaldehyde

Jones reagent

→

12

수율 93.0%

3-hydroxyestra-1,3,5(10)-trien-17-one-4-carboxaldehyde

수율 93.0%

용매

acetone

반응 조건

후처리

1. 1
   기타quenched with 2-propanol
2. 2
   추출extracted with EtOAc
3. 3
   세척The combined organic layers were washed with H2O
4. 4
   건조with saturated aqueous NaCl, and dried (Na2SO4)
5. 5
   여과The desiccant was filtered
6. 6
   기타the solvent was evaporated at reduced pressure
7. 7
   기타The residue was purified by column chromatography (silica gel)

실험 절차

To a solution of 3,17β-dihydroxyestra-1,3,5(10)-triene-4-carboxaldehyde (2b, 0.300 g, 1.0 mmol) in acetone (10 mL) was added Jones reagent (0.50 mL) at 0° C. The reaction mixture was stirred for 10 min, quenched with 2-propanol, and extracted with EtOAc. The combined organic layers were washed with H2O, then with saturated aqueous NaCl, and dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:THF (4:1→2:1, v/v) to afford 0.276 g of 12 (93% yield), m.p. 234°-237° C.

출처