Sodium Chloride → 3,3-(Ethylenedioxy)-11beta-[4'-(methylthio)[1,1'-biphenyl]-4-yl]-5-estren-17-one

HRID 1654422Notes

Reaction equation

HRID 1654422 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.C(=O)([O-])[O-].[Na+].[Na+].[CH3:44][S:45][C:46]1[CH:51]=[CH:50][C:49](B(O)O)=[CH:48][CH:47]=1.[Cl-].[Na+]>C1(C)C=CC=CC=1.C(O)C.[Cl-].[Li+]>[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[C@@H:16]([C:21]3[CH:22]=[CH:23][C:24]([C:49]5[CH:50]=[CH:51][C:46]([S:45][CH3:44])=[CH:47][CH:48]=5)=[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:36]1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 867486213,3-(Ethylenedioxy)-11beta-(4-trifluoromethylsulfonyloxyphenyl)-5-estren-17-one

Product 1

HCID 677883793,3-(Ethylenedioxy)-11beta-[4'-(methylthio)[1,1'-biphenyl]-4-yl]-5-estren-17-oneYield 100.2%

Reagents, catalysts & solvents 3

HCID 433294Lithium ChlorideCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

1.73 g of 3,3-(ethylenedioxy)-11β-(4-trifluoromethylsulfonyloxyphenyl)-5-estren-17-one is dissolved in a mixture of 17 ml of toluene and 5 ml of ethanol and mixed in succession with 37 mg of palladiumtetrakistriphenylphosphine, 0.28 mg of lithium chloride, 4 ml of 2 m sodium carbonate solution and 0.7 g of [4-(methylthio)phenyl]boronic acid. The reaction mixture is then stirred for 6 hours at 95° 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, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane. 1.65 g of the title compound is obtained as white foam.

Workup

  1. temperaturecooled to room temperature
  2. customThe organic phase is separated
  3. washwashed in succession with 5% sodium hydroxide solution and water
  4. customdried 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-093094baf16b4c1d86ad2ac6f54b57b2
Source dataset
uspto-grants-1995_04
Patent number
US05405979

Reaction notes

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