Isopropenyl acetate → 2-Methoxy-3,17-diacetoxyestra-1,3,5(10),14,16-pentaene

HRID 1357475

Reaktionsgleichung

Reaktionsgleichung von HRID 1357475
O.C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH3:13][O:14][C:15]1[C:16]([OH:34])=[CH:17][C:18]2[CH2:19][CH2:20][C@@H:21]3[C@@H:30]([C:31]=2[CH:32]=1)[CH2:29][CH2:28][C@@:26]1([CH3:27])[C@H:22]3[CH:23]=[CH:24][C:25]1=[O:33].[C:35](OC(C)=C)(=[O:37])[CH3:36].[C:42](OC(=O)C)(=[O:44])[CH3:43]>C(Cl)Cl.CC(C)=O>[CH3:13][O:14][C:15]1[C:16]([O:34][C:42](=[O:44])[CH3:43])=[CH:17][C:18]2[CH2:19][CH2:20][C@@H:21]3[C@@H:30]([C:31]=2[CH:32]=1)[CH2:29][CH2:28][C@@:26]1([CH3:27])[C:22]3=[CH:23][CH:24]=[C:25]1[O:33][C:35](=[O:37])[CH3:36]

Komponenten

7

Edukt 4

HCID 7916Isopropenyl acetateHCID 7918Acetic AnhydrideHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 211357012-Methoxyestra-1,3,5(10),15-tetraen-3-ol-17-one

Produkt 1

HCID 113265312-Methoxy-3,17-diacetoxyestra-1,3,5(10),14,16-pentaeneAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under nitrogen, toluenesulfonic acid monohydrate (0.1 g, 0.53 mmol) was added to a solution of 2-Methoxyestra-1,3,5(10),15-tetraen-3-ol-17-one prepared in Example 3 (0.25 g, 0.84 mmol), isopropenyl acetate (5 mL, 45.15 mmol) and acetic anhydride (5 mL, 53 mmol) and the mixture was heated to reflux for 6 h. At the end of that time, analysis by tlc (2% acetone in CH2Cl2) indicated a complete reaction. The reaction was cooled to room temperature, poured into ice water (˜100 mL) and stirred for 1 h. The mixture was extracted with methylene chloride (3x). The organic fractions were washed with water (1x), saturated sodium bicarbonate solution (1x) and water (1x), filtered through anhydrous sodium sulfate, combined and concentrated in vacuo. The residue was crystallized from methanol to give the pure diacetate (17) (0.259 g, 80.8%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 h
  3. customa complete reaction
  4. extractionThe mixture was extracted with methylene chloride (3x)
  5. washThe organic fractions were washed with water (1x), saturated sodium bicarbonate solution (1x) and water (1x)
  6. filtrationfiltered through anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-b12bbfe5a68b46f382406ef47271b6fb
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593321B2

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