4-Formyl-17beta-estradiol → 4-Formylestrone

HRID 343305

Reaktionsgleichung

Reaktionsgleichung von HRID 343305
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C@@H:11]([OH:20])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[C:3]=1[CH:21]=[O:22].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[C:3]=1[CH:21]=[O:22]

Komponenten

4

Edukt 2

HCID 117223424-Formyl-17beta-estradiolHCID 131709961Jones' reagent

Produkt 1

HCID 143343274-FormylestroneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customquenched with 2-propanol
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O
  4. dry with materialwith saturated aqueous NaCl, and dried (Na2SO4)
  5. filtrationThe desiccant was filtered
  6. customthe solvent was evaporated at reduced pressure
  7. customThe residue was purified by column chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-ce95a65df00c40ad932a9a570aa9ef88
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861388

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