Water → HCID 86734259, compound

HRID 1973495Notes

Reaction equation

HRID 1973495 reaction equation
[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:22][C@H:21]([OH:23])[C@H:20]4[C@@H:11]([CH2:12][CH2:13][C:14]5[CH:15]=[C:16]([OH:24])[CH:17]=[CH:18][C:19]=54)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1.[C:25](=O)([O-])[O-].[K+].[K+].O>CO.CI>[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:22][C@H:21]([OH:23])[C@H:20]4[C@@H:11]([CH2:12][CH2:13][C:14]5[CH:15]=[C:16]([O:24][CH3:25])[CH:17]=[CH:18][C:19]=54)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86734260HCID 86734260, compound

Product 1

HCID 86734259HCID 86734259, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6328Methyl iodideSolvent

Procedure

A mixture of 15 g of 17-ethylenedioxyestra-1,3,5(10) trien-3,11β-diol and 30 g of anhydrous potassium carbonate in 75 ml of methanol and 60 ml of methyl iodide is stirred and heated under reflux for 3 hours. The mixture is then cooled and diluted by the addition of 200 ml of water. The methanol and methyl iodide are removed by distillation under reduced pressure and the aqueous residue is extracted twice with methylene chloride. The combined organic extracts are washed with saturated sodium chloride solution and dried over sodium sulfate. Removal of the solvent gives a residue which is crystallized from ether to yield 17-ethylenedioxy-11β-hydroxy-3-methoxyestra-1,3,5(10)-triene, m.p. 125° - 126° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture is then cooled
  4. customThe methanol and methyl iodide are removed by distillation under reduced pressure
  5. extractionthe aqueous residue is extracted twice with methylene chloride
  6. washThe combined organic extracts are washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customRemoval of the solvent
  9. customgives a residue which
  10. customis crystallized from ether

Sources & evidence

ORD record
ord-eb7dc83fc0d74adbb0bcf914d1304d6b
Source dataset
uspto-grants-1976_12
Patent number
US03997574

Reaction notes

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