Dimethylformamide → 3,3-(Ethylenedioxy)-11beta-(4-vinylphenyl)-5-estren-17-one

HRID 1654419노트

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HRID 1654419 반응식
[CH2:1]1[CH2:37][O:36][C:3]2([CH2:20][CH2:19][C@H:18]3[C:5](=[CH:6][CH2:7][C@@H:8]4[C@@H:17]3[C@@H:16]([C:21]3C=CC(OS(C(F)(F)F)(=O)=O)=CC=3)[CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C:12]3=[O:35])[CH2:4]2)[O:2]1.[Cl-].[Li+].[CH2:40]([C:44]([Sn])=[C:45]([CH2:50]CCC)[CH2:46][CH2:47]CC)CCC.[CH3:55]N(C)C=O>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:37]1[CH2:1][O:2][C:3]2([CH2:20][CH2:19][C@H:18]3[C:5](=[CH:55][CH2:21][C@@H:16]4[C@@H:17]3[C@@H:8]([C:7]3[CH:6]=[CH:50][C:45]([CH:46]=[CH2:47])=[CH:44][CH:40]=3)[CH2:9][C@@:13]3([CH3:14])[C@H:15]4[CH2:10][CH2:11][C:12]3=[O:35])[CH2:4]2)[O:36]1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 53438229Tri(butyl)vinyltinHCID 867486213,3-(Ethylenedioxy)-11beta-(4-trifluoromethylsulfonyloxyphenyl)-5-estren-17-one

생성물 1

HCID 677890453,3-(Ethylenedioxy)-11beta-(4-vinylphenyl)-5-estren-17-one

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

1.7 g of 3,3-(ethylenedioxy)-11β-(4-trifluoromethylsulfonyloxyphenyl)-5-estren-17-one is dissolved in 25 ml of absolute dimethylformamide and mixed with 270 mg of lithium chloride and 190 mg of tetrakistriphenylphosphinepalladium. After five more minutes of stirring, the reaction mixture is mixed with 1.15 ml of tributylvinyltin, stirred for 1 hour at 110° C. under protective gas, cooled to room temperature and diluted with ethyl acetate. After filtration on Celite and washing of the filter residue with ethyl acetate, the organic phase is washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. Chromatography of the residue on aluminum oxide (neutral, stage II) with a mixture of ethyl acetate/hexane yields 1.2 g of 3,3-(ethylenedioxy)-11β-(4-vinylphenyl)-5-estren-17-one as white foam.

후처리

  1. stirringstirred for 1 hour at 110° C. under protective gas
  2. filtrationAfter filtration on Celite
  3. washwashing of the filter residue with ethyl acetate
  4. washthe organic phase is washed with saturated sodium chloride solution
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation in a vacuum
  7. additionChromatography of the residue on aluminum oxide (neutral, stage II) with a mixture of ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-77d1da54283649fe8e0dbed8110395d4
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05405979

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