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

HRID 1606382Notes

Reaction equation

HRID 1606382 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 (Chamberlin et al., J. Amer. Chem. Soc., 1951, 73, 2396) (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 (ca. 100 g.). The material obtained was crystallised from acetone petroleum to give pure title compound (17.65 g.), as small plates, m.p. 217.5°, [α]D +82.9° (c 1.1), λmax. 234 nm. (ε 10,100).

Workup

  1. filtrationthe product filtered off
  2. dissolutionThe crude material was dissolved in chloroform
  3. filtrationfiltered through a column of grade III neutral alumina (ca. 100 g.)
  4. customThe material obtained
  5. customwas crystallised from acetone petroleum

Sources & evidence

ORD record
ord-89775ab3fc2043ffa97a68a105710b62
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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