Methanol → 17beta-Cyclohexylcarbonyl-estra-1,3,5(10)-triene-3-carboxylic Acid

HRID 53449Notes

Reaction equation

HRID 53449 reaction equation
C[O:2][C:3]([C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([C:23]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:24])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].O.CO>C(OCC)(=O)C>[CH:25]1([C:23]([C@H:14]2[CH2:13][CH2:12][C@H:11]3[C@H:10]4[C@H:19]([CH2:18][CH2:17][C@:15]23[CH3:16])[C:20]2[CH:21]=[CH:22][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[CH2:8][CH2:9]4)=[O:24])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 67707002HCID 67707002, compound

Product 1

HCID 5409548217beta-Cyclohexylcarbonyl-estra-1,3,5(10)-triene-3-carboxylic AcidYield 8,200%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl-17β-cyclohexylcarbonyl-estra-1,3,5(10)-triene-3-carboxylate (0.14 g, 0.34 mmol), K2CO3 (0.2 g, 1.45 mmol), water (3.0 mL) and methanol (30 mL) was heated at reflux overnight. The reaction mixture was then concentrated. The residue was diluted with water, acidified with dilute HCl and extracted with ethyl acetate. The organic extract was washed with brine, dried, and concentrated. The resulting solid was washed with CH3CN and isolated by filtration from boiling ethyl acetate to give, 0. 11 g of the title compound. mp 280°-285° C. (softened at 260° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was then concentrated
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with brine
  8. customdried
  9. concentrationconcentrated
  10. washThe resulting solid was washed with CH3CN
  11. customisolated by filtration
  12. customto give

Sources & evidence

ORD record
ord-20dec9601cad4b28adb26edc2aa51fff
Source dataset
uspto-grants-1997_04
Patent number
US05618806

Reaction notes

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