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

HRID 1654419Notes

Reaction equation

HRID 1654419 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-77d1da54283649fe8e0dbed8110395d4
Source dataset
uspto-grants-1995_04
Patent number
US05405979

Reaction notes

Loading…