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

HRID 23360

Reaktionsgleichung

Reaktionsgleichung von HRID 23360
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 (3×). The organic fractions were washed with water (1×), saturated sodium bicarbonate solution (1×) and water (1×), 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 (3×)
  5. washThe organic fractions were washed with water (1×), saturated sodium bicarbonate solution (1×) and water (1×)
  6. filtrationfiltered through anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-3a1850c7645c4ec2930d5b5153faa06f
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852710B2

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