Sodium methanethiolate → HCID 67576803, compound

HRID 1708590Notes

Reaction equation

HRID 1708590 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:25]([C:27]4[CH:32]=[CH:31][C:30]([OH:33])=[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:12]1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 67788990HCID 67788990, compound

Product 1

HCID 67576803HCID 67576803, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17,17-bis-(ethylenedioxy)11-(4-methoxyphenyl)-5,9(11)-estradiene 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)-11-(4-hydroxyphenyl)-5,9(11)-estradiene is obtained as white foam.

Workup

  1. temperaturethe reaction mixture is refluxed for 3 hours
  2. temperatureAfter cooling it
  3. additionis 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-fd32308f2bd34b9c85f6b3f1da028df4
Source dataset
uspto-grants-1994_10
Patent number
US05359054

Reaction notes

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