Potassium Hydroxide → 3beta-Hydroxy-5alpha-pregn-16-ene-11,20-dione

HRID 1606484Notes

Reaction equation

HRID 1606484 reaction equation
C([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[C:20](=[O:26])[CH2:19][C@@:18]2([CH3:27])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=O)C.[OH-].[K+]>O1CCOCC1.O>[OH:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[C:20](=[O:26])[CH2:19][C@@:18]2([CH3:27])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 2271023beta-Hydroxy-5alpha-pregn-16-ene-11,20-dione 3-acetate

Product 1

HCID 705834293beta-Hydroxy-5alpha-pregn-16-ene-11,20-dioneYield 77.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3β-acetoxy-5α-pregn-16-ene-11,20-dione (25.7 g.) in dioxan (500 ml.) was treated with potassium hydroxide (10 g.) and water (250 ml.) and the mixture allowed to stand at room temperature for 1 hour. After a further 1 hour at 40° the mixture was diluted with water and the product filtered off. The crude material was dissolved in chloroform and filtered through a column of grade III neutral alumina. Crystallisation from acetone-petrol gave pure 3β-hydroxy-5α-pregn-16-ene-11,20-dione (17.65 g.) as small plates m.p. 217.5°, [α]D + 82.9°. (c 1.1)

Workup

  1. filtrationthe product filtered off
  2. dissolutionThe crude material was dissolved in chloroform
  3. filtrationfiltered through a column of grade III neutral alumina
  4. customCrystallisation from acetone-petrol

Sources & evidence

ORD record
ord-b4c351d2c92347b19cffbfd41a43a45b
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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