Hydrochloric Acid → HCID 9821134, compound

HRID 1654416Notes

Reaction equation

HRID 1654416 reaction equation
C1CO[C:8]23OCCO[C:3]2([C@:4]2([CH2:26][C@H:25]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[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.Cl.C(=O)(O)[O-:37].[Na+]>CC(C)=O>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([C@H:25]2[CH2:26][C@@:4]3([CH3:5])[C@@H:6]([CH2:7][CH2:8][C:3]3=[O:2])[C@H:15]3[C@H:24]2[C@@H:23]2[C:18]([CH2:17][CH2:16]3)=[CH:19][C:20](=[O:37])[CH2:21][CH2:22]2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86748619HCID 86748619, compound

Product 1

HCID 9821134HCID 9821134, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

17,17-bis-(ethylenedioxy)-11β-(4-methoxyphenyl)-5-estrene is dissolved in 50 ml of acetone and mixed under protective gas with 2.5 ml of 4 n aqueous hydrochloric acid. After three hours of stirring at room temperature and one hour at 40° C., the reaction mixture is poured on cold saturated sodium bicarbonate solution and the aqueous phase is extracted several times with methylene chloride. The combined organic phases are 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. 683 mg of 11β-(4-methoxyphenyl)-4-estrene-3,17-dione is obtained as white foam.

Workup

  1. extractionthe aqueous phase is extracted several times with methylene chloride
  2. customThe combined organic phases are dried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customThe residue is chromatographed on silica gel-with a mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-f9f13df5336a491ebf11eef47c933d68
Source dataset
uspto-grants-1995_04
Patent number
US05405979

Reaction notes

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