Sodium Chloride → HCID 67576704, compound

HRID 1455911Notes

Reaction equation

HRID 1455911 reaction equation
[CH2:1]1[CH2:39][O:38][C:3]2([CH2:20][CH2:19][C@H:18]3[C@@:5]([OH:37])([C@H:6]([CH3:36])[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+].C(B(CC)[C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1)C.[Cl-].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH2:1]1[CH2:39][O:38][C:3]2([CH2:20][CH2:19][C@H:18]3[C@@:5]([OH:37])([C@H:6]([CH3:36])[CH2:7][C@@H:8]4[C@@H:17]3[C@@H:16]([C:21]3[CH:22]=[CH:23][C:24]([C:51]5[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=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:2]1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 6428513-(Diethylboryl)pyridineHCID 86753382HCID 86753382, compound

Product 1

HCID 67576704HCID 67576704, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

10 g of the 3,3-(ethylenedioxy)-5α-hydroxy-6β-methyl-11β-(4-trifluoromethylsulphonyloxyphenyl)-oestran-17-one prepared in accordance with the directions given in Example 4 e) are dissolved in a mixture of 80 ml of toluene and 35 ml of ethanol and 1 g of palladium tetrakistriphenylphosphine, 1.47 g of lithium chloride, 22.5 ml of 2M sodium carbonate solution and 2.8 g of diethyl-(3-pyridyl)-borane are added in succession. The reaction mixture is then stirred at 110° C. for 3 hours and cooled to room temperature, and saturated sodium chloride solution is added. The organic phase is removed, washed in succession with 5% sodium hydroxide solution and water, dried over sodium sulphate and concentrated in vacuo. The residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane. 7.53 g of 3,3-(ethylenedioxy)-5α-hydroxy-6β-methyl-11β-[4-(3-pyridyl)-phenyl]-oestran-17-one are obtained in the form of a white foam.

Workup

  1. additionare added in succession
  2. temperaturecooled to room temperature
  3. customThe organic phase is removed
  4. washwashed in succession with 5% sodium hydroxide solution and water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-8a38db43d9154c56b8e3f8473158d915
Source dataset
uspto-grants-1998_12
Patent number
US05843931

Reaction notes

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