Boron trifluoride etherate → 3-Methoxy-7alpha-(2-propenyl)estra-1,3,5(10)-trien-17beta-ol

HRID 1582816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582816
C([SiH](CC)CC)C.B(F)(F)F.CCOCC.[OH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]2[C@H:24]3[C@H:33]([CH2:34][CH2:35][C@:19]12[CH3:20])[C:32]1[CH:31]=[CH:30][C:29]([O:36][CH3:37])=[CH:28][C:27]=1[C:26](=O)[C@H:25]3[CH2:39][CH:40]=[CH2:41].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:37][O:36][C:29]1[CH:30]=[CH:31][C:32]2[C@@H:33]3[C@H:24]([C@H:21]4[C@@:19]([CH2:35][CH2:34]3)([CH3:20])[C@@H:18]([OH:17])[CH2:23][CH2:22]4)[C@H:25]([CH2:39][CH:40]=[CH2:41])[CH2:26][C:27]=2[CH:28]=1

Komponenten

6

Edukt 4

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 6941500617beta-Hydroxy-3-methoxy-7alpha-(2-propenyl)estra-1,3,5(10)-trien-6-one

Produkt 1

HCID 694148073-Methoxy-7alpha-(2-propenyl)estra-1,3,5(10)-trien-17beta-olAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylsilane (5 ml) and boron trifluoride diethyl etherate (5 ml) were added to a solution of 17β-hydroxy-3-methoxy-7α-(2-propenyl)estra-1,3,5(10)-trien-6-one (1.0 g, 2.9 mmol) in dichloromethane (20 mL) at 0° C. The resulting mixture was warmed to room temperature and stirred for 18 hours. After the reaction was completed, 10% aqueous potassium carbonate was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then filtered. After concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to give 3-methoxy-7α-(2-propenyl)estra-1,3,5(10)-trien-17β-ol (935 mg, Yield 98%).

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationAfter concentration under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-ff0ccbc9e7024b25818fe3011591c61b
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06737417B2

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