Water → HCID 88471420, compound

HRID 654430Notes

Reaction equation

HRID 654430 reaction equation
C[Si](C)(C)[C:3]#[C:4][CH2:5][C@:6]1([OH:34])[CH:11]=[CH:10][C@H:9]2[C@H:12]3[C:21]([C@@H:22]([C:24]4[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[CH:26][CH:25]=4)[CH2:23][C@:7]12[CH3:8])=[C:20]1[C:15](=[CH:16][C:17](=[O:33])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH2:5]([C@:6]1([OH:34])[CH:11]=[CH:10][C@H:9]2[C@H:12]3[C:21]([C@@H:22]([C:24]4[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[CH:26][CH:25]=4)[CH2:23][C@:7]12[CH3:8])=[C:20]1[C:15](=[CH:16][C:17](=[O:33])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)[C:4]#[CH:3]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 131717467HCID 131717467, compound

Product 1

HCID 88471420HCID 88471420, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

350 mg of 17-(3-trimethylsilyl-prop-2-inyl)-17β-hydroxy-11β-(4-acetylphenyl)-4,9,15-estratrien-3-one is dissolved in methanol and stirred at 23° C. for 1.5 hours after addition of 387 mg of potassium carbonate. This is poured into water and extracted with acetic ester. The combined organic phases are dried over sodium sulphate and concentrated in vacuo. The residue is chromatographed with a mixture of hexane/acetic ester over silica gel. 205 mg of the title compound is isolated as white foam. Crystallisation from ether yields 176 mg of the title compound.

Workup

  1. extractionextracted with acetic ester
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue is chromatographed with a mixture of hexane/acetic ester over silica gel

Sources & evidence

ORD record
ord-af89974f51db434b84f1ce6de41f3a0d
Source dataset
uspto-grants-1992_07
Patent number
US05132299

Reaction notes

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