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

HRID 1357475노트

반응식

HRID 1357475 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 113265312-Methoxy-3,17-diacetoxyestra-1,3,5(10),14,16-pentaene수율 80.8%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b12bbfe5a68b46f382406ef47271b6fb
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06593321B2

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