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

HRID 53447Notes

Reaction equation

HRID 53447 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, K2CO3, water and methanol is heated at reflux for 5 h. The volatiles are then removed at reduced pressure and the residue is diluted with water, acidified with dilute aqueous HCl, and extracted with EtOAc. The organic extract is washed with water and brine, dried, and evaporated to yield the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 5 h
  3. customThe volatiles are then removed at reduced pressure
  4. additionthe residue is diluted with water
  5. extractionextracted with EtOAc
  6. extractionThe organic extract
  7. washis washed with water and brine
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-e1717645044a464f8aa75e660cd0f8f3
Source dataset
uspto-grants-1997_04
Patent number
US05618806

Reaction notes

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