Sodium Chloride → HCID 67788990, compound

HRID 1708589Notes

Reaction equation

HRID 1708589 reaction equation
[CH2:1]1[CH2:14][O:13][C:8]23[O:9][CH2:10][CH2:11][O:12][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][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:2]1.[Cl-].[Li+].C(=O)([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>[CH2:11]1[CH2:10][O:9][C:8]23[O:13][CH2:14][CH2:1][O:2][C:3]2([C@:4]2([CH2:26][C:25]([C:48]4[CH:49]=[CH:50][C:45]([O:44][CH3:43])=[CH:46][CH:47]=4)=[C:24]4[C@@H:15]([CH2:16][CH:17]=[C:18]5[C@@H:23]4[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])[O:12]1

Participants

8

Reactant 5

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

Product 1

HCID 67788990HCID 67788990, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

21.6 g (42.6 mmol) of 3,3; 17,17-bis- (ethylenedioxy) -11-trifluoromethylsulfonyloxy-5,9(11)-estradiene is disson, red 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 m sodium carbonate solution and 7.2 g (46.8 mmol) of 4-methoxyphenyl boronic acid. The reaction mixture is then stirred for 2 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 3,3;17,17-bis-(ethylenedioxy)11-(4-methoxyphenyl)-5,9(11)-estradiene 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-2d5fe7b50ebb42ae934c0e5e4814ee30
Source dataset
uspto-grants-1994_10
Patent number
US05359054

Reaction notes

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