Sodium methanethiolate → HCID 86748620, compound

HRID 1455912Notes

Reaction equation

HRID 1455912 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]([C:27]4[CH:32]=[CH:31][C:30]([O:33]C)=[CH:29][CH:28]=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:2]1.C[S-].[Na+]>CN(C)C=O>[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@H:25]([C:27]4[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=4)[C@H: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

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 67788990HCID 67788990, compound

Product 1

HCID 86748620HCID 86748620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

130 g of the compound prepared in Example 1 c) are dissolved in 1.4 l of absolute dimethylformamide, 7.81 g of sodium methanethiolate are added and the reaction mixture is heated under reflux for 3 hours. The mixture is cooled and then poured onto water and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed repeatedly with saturated sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. The residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane and 76.9 g of 3,3;17,17-Bis-(ethylenedioxy)-11β-(4-hydroxyphenyl)-5-oestrene are obtained in the form of a white foam.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture is cooled
  4. additionpoured onto water
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. washThe combined organic phases are washed repeatedly with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane and 76.9 g of 3,3

Sources & evidence

ORD record
ord-b27bed480e12485199c9897491d70eb6
Source dataset
uspto-grants-1998_12
Patent number
US05843931

Reaction notes

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