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Trimethyl orthoformate → 3-Ethylenedioxy-11beta-fluoro-7alpha-methylestr-5(10)-en-17beta-ol

HRID 900678
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인쇄 미리보기

반응식

HRID 900678 반응식
[CH:1]([O:6][CH3:7])(OC)OC.O.[C:9]1(C)C=CC(S(O)(=O)=O)=CC=1.[F:20][C@H:21]1[CH2:38][C@@:36]2([CH3:37])[C@@H:32]([CH2:33][CH2:34][C@@H:35]2[OH:39])[C@H:31]2[C@H:22]1[C@@H:23]1[C:28]([CH2:29][C@H:30]2[CH3:40])=[CH:27][C:26](=[O:41])C[CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(OCC)(=O)C.C(O)CO>[CH2:9]1[CH2:7][O:6][CH:1]2[CH:26]([CH2:27][C:28]3[CH2:29][C@@H:30]([CH3:40])[C@@H:31]4[C@@H:22]([C:23]=3[CH2:24]2)[C@@H:21]([F:20])[CH2:38][C@@:36]2([CH3:37])[C@H:32]4[CH2:33][CH2:34][C@@H:35]2[OH:39])[O:41]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 990463811beta-Fluoro-17beta-hydroxy-7alpha-methylestr-4-en-3-one

생성물 1

HCID 865974503-Ethylenedioxy-11beta-fluoro-7alpha-methylestr-5(10)-en-17beta-ol

시약·촉매·용매 3

HCID 174
Ethylene Glycol
용매
HCID 6344Dichloromethane용매
HCID 8857Ethyl Acetate용매

실험 절차

3.63 ml of ethylene glycol and 1.82 ml of trimethyl orthoformate and 23.6 ml of para-toluenesulfonic acid hydrate were added to a solution of 500 mg of 11β-fluoro-17β-hydroxy-7α-methyl-estr-4-en-3-one (I) in 6.35 ml of dichloromethane. The reaction mixture was stirred for 20 hours at room temperature. Then, it was mixed with sodium carbonate solution, diluted with ethyl acetate, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 170 mg of 3-ethylenedioxy-11β-fluoro-7α-methylestr-5(10)-en-17β-ol (C), which contained portions of double-bond-isomeric 3-ethylenedioxy-11β-fluoro-7α-methylestr-5-en-17β-ol (C), was obtained.

후처리

  1. washwashed neutral
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with hexane/ethyl acetate
  5. customwas obtained

출처 및 근거

ORD 기록
ord-855d177f12974593abd7ebbbd9a30865
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07361645B2

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