Sodium Chloride → 3,3-(Ethylenedioxy)-11-[4-(3-pyridyl)phenyl]-5-estren-17-one

HRID 1654420Notes

Reaction equation

HRID 1654420 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]3[CH:26]=[CH:25][C:24](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:22]=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+].C(=O)([O-])[O-].[Na+].[Na+].[CH2:46](B(CC)[C:49]1[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=1)[CH3:47].[Cl-].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH2:37]1[CH2:1][O:2][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[CH:16]([C:21]3[CH:26]=[CH:25][C:24]([C:49]5[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=5)=[CH:23][CH:22]=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:36]1.[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[CH:16]([C:21]3[CH:22]=[CH:23][C:24]([CH2:46][CH3:47])=[CH:25][CH:26]=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

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 6428513-(Diethylboryl)pyridineHCID 867486213,3-(Ethylenedioxy)-11beta-(4-trifluoromethylsulfonyloxyphenyl)-5-estren-17-one

Product 2

HCID 543245133,3-(Ethylenedioxy)-11-[4-(3-pyridyl)phenyl]-5-estren-17-oneHCID 543698183,3-(Ethylenedioxy)-11-(4-ethylphenyl)-5-estren-17-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

4.92 g (9.1 mmol) of 3,3-(ethylenedioxy)-11β-(4-trifluoromethylsulfonyloxyphenyl)-5-estren-17-one is dissolved in a mixture of 80 ml of toluene and 35 ml of ethanol and mixed in succession with 0.53 g of palladiumtetrakistriphenylphosphine, 0.77 g of lithium chloride, 11 ml of 2 molar sodium carbonate solution and 1.47 g (10 mmol) of diethyl(3-pyridyl)borane. The reaction mixture is then stirred for one hour at 110° C., cooled to room temperature and mixed with saturated sodium chloride solution. The organic phase is separated, washed in succession with 5% sodium hydroxide solution and water, washed on sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane. 3.55 g of 3,3-(ethylenedioxy)-11-[4-(3-pyridyl)phenyl]-5-estren-17-one and 382 mg of 3,3-(ethylenedioxy)-11-(4-ethylphenyl)-5-estren-17-one are obtained as white foams.

Workup

  1. temperaturecooled to room temperature
  2. customThe organic phase is separated
  3. washwashed in succession with 5% sodium hydroxide solution and water
  4. washwashed on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-b26cff07ec494f5ca5488afae5ebe404
Source dataset
uspto-grants-1995_04
Patent number
US05405979

Reaction notes

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