Sodium Chloride → HCID 9821134, compound

HRID 1654413Notes

Reaction equation

HRID 1654413 reaction equation
C1CO[C:8]23OCCO[C:3]2([C@:4]2([CH2:26][C:25](OS(C(F)(F)F)(=O)=O)=[C:24]4[C@@H:15]([CH2:16][CH:17]=[C:18]5[C@@H:23]4[CH2:22][CH2:21]C[CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1.[Cl-].[Li+].[C:37](=[O:40])([O-])[O-].[Na+].[Na+].[CH3:43][O:44][C:45]1[CH:50]=[CH:49][C:48](B(O)O)=[CH:47][CH:46]=1.[Cl-].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH3:43][O:44][C:45]1[CH:50]=[CH:49][C:48]([C@H:25]2[CH2:26][C@@:4]3([CH3:5])[C@@H:6]([CH2:7][CH2:8][C:3]3=[O:2])[C@H:15]3[C@H:24]2[C@@H:23]2[C:18]([CH2:17][CH2:16]3)=[CH:19][C:37](=[O:40])[CH2:21][CH2:22]2)=[CH:47][CH:46]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 433294Lithium ChlorideHCID 86748214HCID 86748214, compound

Product 1

HCID 9821134HCID 9821134, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

17,17-bis-(ethylenedioxy)-11-trifluoromethylsulfonyloxy-5,9(11)-estradiene is dissolved in a mixture of 360 ml of toluene and 170 ml of ethanol and mixed in succession with 2.5 g of palladiumtetrakistriphenylphosphine, 3.6 g of lithium chloride, 55 ml of 2 molar sodium carbonate solution and 7.2 g (46.8 mmol) of 4-methoxyphenyl boronic acid. The reaction mixture is then stirred for two 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. 19.2 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-d583829b7cfe479c9b9dbdb358ba2cf3
Source dataset
uspto-grants-1995_04
Patent number
US05405979

Reaction notes

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