Methanol → HCID 68147389, compound

HRID 1606291Notes

Reaction equation

HRID 1606291 reaction equation
[CH3:1][O:2][C:3]1[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]([O:21]C(=O)C)[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:25][CH3:26])[CH:4]=1.CO.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[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]([OH:21])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:25][CH3:26])[CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 70617822HCID 70617822, compound

Product 1

HCID 68147389HCID 68147389, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.5 g. of rac.-1,3-dimethoxy-17β-acetoxy-8α-estra-1,3,5(10)-triene is saponified under N2 in 100 ml. of methanol with 13 ml. of aqueous potash solution (10%) by heating for 1.5 hours under reflux. After cooling, the mixture is gently neutralized with glacial acetic acid, concentrated to half its volume, precipitated into ice water/NaCl, and worked up, thus obtaining 4.1 g. of crude product. By recrystallization of 500 mg. from methanol, 330 mg. of final product is obtained, m.p. 153/153.5°-154°C.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. concentrationconcentrated to half its volume
  4. customprecipitated into ice water/NaCl
  5. customthus obtaining 4.1 g
  6. customBy recrystallization of 500 mg

Sources & evidence

ORD record
ord-9f19184b6be34e3781fb727d09ef4cbe
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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