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

HRID 1582816노트

반응식

HRID 1582816 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 694148073-Methoxy-7alpha-(2-propenyl)estra-1,3,5(10)-trien-17beta-ol수율 98.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ff0ccbc9e7024b25818fe3011591c61b
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06737417B2

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