Reaction #81727

Reaction equation

methyl-17β-cyclohexylcarbonyl-estra-1,3,5(10)-triene-3-carboxylate

K2CO3

water

methanol

→

title compound

17β-Cyclohexylcarbonyl-estra-1,3,5(10)-triene-3-carboxylic Acid

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux overnight
3. 3
   ConcentrationThe reaction mixture was then concentrated
4. 4
   workup.ADDITIONThe residue was diluted with water
5. 5
   Extractionextracted with ethyl acetate
6. 6
   ExtractionThe organic extract
7. 7
   Washwas washed with brine
8. 8
   Otherdried
9. 9
   Concentrationconcentrated
10. 10
    WashThe resulting solid was washed with CH3CN
11. 11
    Otherisolated by filtration
12. 12
    Otherto give

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.).

Source