Sodium methanethiolate → HCID 86748620, compound

HRID 1654418Notes

Reaction equation

HRID 1654418 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@H:25]([C:27]4[CH:32]=[CH:31][C:30]([O:33]C)=[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: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 86748619HCID 86748619, compound

Product 1

HCID 86748620HCID 86748620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17,17-bis-(ethylenedioxy)-11β-(4-methoxyphenyl)-5-estrene is dissolved in 100 ml of absolute dimethylformamide, mixed with 5.6 g of sodium methanethiolate and the reaction mixture is refluxed for 3 hours. After cooling, it is poured on water and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed several times with saturated sodium chloride solution, 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 and 8.67 g of 3,3;17,17-bis-(ethylenedioxy)-11β-(4-hydroxyphenyl)-5-estrene is obtained as white foam.

Workup

  1. temperaturethe reaction mixture is refluxed for 3 hours
  2. temperatureAfter cooling
  3. additionit is poured on water
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. washThe combined organic phases are washed several times with saturated sodium chloride solution
  6. customdried on sodium sulfate
  7. concentrationconcentrated by evaporation in a vacuum
  8. customThe residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane and 8.67 g of 3,3

Sources & evidence

ORD record
ord-dd4688012e804526876cef271e8bba6b
Source dataset
uspto-grants-1995_04
Patent number
US05405979

Reaction notes

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