Sodium Bicarbonate → HCID 9821134, compound

HRID 1455908Notes

Reaction equation

HRID 1455908 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.C(=O)([O-])[OH:36].[Na+]>CC(C)=O.Cl>[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:36])[CH2:21][CH2:22]2)=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86748619HCID 86748619, compound

Product 1

HCID 9821134HCID 9821134, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
40 °C

Procedure

17,17-bis-(ethylenedioxy)-11β-(4-methoxyphenyl)-5-oestrene are dissolved in 500 ml of acetone and, under an inert gas, 12.5 ml of 4N aqueous hydrochloric acid are added. The reaction mixture is stirred for 2 hours at 40° C. and then poured onto cold saturated sodium hydrogen carbonate solution, and the aqueous phase is extracted repeatedly with methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated in vacuo. The residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane. 12.94 g of 11β-(4-methoxyphenyl)-4-oestrene-3,17-dione are obtained in the form of a white foam.

Workup

  1. additionare added
  2. extractionthe aqueous phase is extracted repeatedly with methylene chloride
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-805a5870e0524cbdbad1f1c4cc0bbad3
Source dataset
uspto-grants-1998_12
Patent number
US05843931

Reaction notes

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