Water → 17beta-Benzoyl-estra-1,3,5(10)-triene-3-carboxylic Acid

HRID 53446Notes

Reaction equation

HRID 53446 reaction equation
[C:1]([C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:24]([CH2:25][CH2:26][C@:10]12[CH3:11])[C:23]1[CH:22]=[CH:21][C:20]([C:27]([O:29]C)=[O:28])=[CH:19][C:18]=1[CH2:17][CH2:16]3)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].O>CO>[C:1]([C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:24]([CH2:25][CH2:26][C@:10]12[CH3:11])[C:23]1[CH:22]=[CH:21][C:20]([C:27]([OH:29])=[O:28])=[CH:19][C:18]=1[CH2:17][CH2:16]3)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 54345982Methyl 17beta-benzoyl-estra-1,3,5(10)-triene-3-carboxylate

Product 1

HCID 988660117beta-Benzoyl-estra-1,3,5(10)-triene-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 17β-benzoyl-estra-1,3,5(10)-triene-3-carboxylate (60 mg, 0.15 mmol), K2CO3 (60 mg, 0.44 mmol), water (1 mL), and methanol (9 mL) was heated at reflux for 5 h. The volatiles were then removed at reduced pressure and the residue was diluted with water, acidified with dilute aqueous HCl, and extracted with EtOAc. The organic extract was washed with water and brine, dried, and evaporated to dryness. Trituration of the residue with acetone and methanol provided the title compound as a white solid, mp 240°-243° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. customThe volatiles were then removed at reduced pressure
  4. additionthe residue was diluted with water
  5. extractionextracted with EtOAc
  6. extractionThe organic extract
  7. washwas washed with water and brine
  8. customdried
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-310ecfb86a4b40d589cf751e84ec977e
Source dataset
uspto-grants-1997_04
Patent number
US05618806

Reaction notes

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