Reaktion #430487

Reaktionsgleichung

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

Jones reagent

→

12

Ausbeute 93.0%

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

Ausbeute 93.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with 2-propanol
2. 2
   Extraktionextracted with EtOAc
3. 3
   WaschenThe combined organic layers were washed with H2O
4. 4
   Trocknenwith saturated aqueous NaCl, and dried (Na2SO4)
5. 5
   FiltrationThe desiccant was filtered
6. 6
   Sonstigethe solvent was evaporated at reduced pressure
7. 7
   SonstigeThe residue was purified by column chromatography (silica gel)

Vorschrift

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.

Quelle