Acetic Acid → 1beta-Methyl-4-androstene-3,17-dione

HRID 2397988Notes

Reaction equation

HRID 2397988 reaction equation
[CH2:1]1[C@@H:3]2[C:4](=[O:22])[CH:5]=[C:6]3[C@:19]([CH3:20])([C@H:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][CH2:7]3.C(O)(=O)C>[Zn].C1C=CC=CC=1>[CH3:1][C@H:2]1[C@@:19]2([CH3:20])[C:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:21])=[CH:5][C:4](=[O:22])[CH2:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 542623781beta,2beta-Methylene-4-androstene-3,17-dione

Product 1

HCID 541757841beta-Methyl-4-androstene-3,17-dione

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

1β,2β-Methylene-4-androstene-3,17-dione, zinc powder, and acetic acid are refluxed for about one hour. Benzene is added, the suspension filtered and the filtrate taken to dryness under vacuum. The residue is chromatographed on silica gel and eluted with methylenechloride. Recrystallization from acetone-hexane yields 1β-methyl-4-androstene-3,17-dione.

Workup

  1. filtrationthe suspension filtered
  2. customThe residue is chromatographed on silica gel
  3. washeluted with methylenechloride
  4. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-d75573b62a85496ab823980756c7e619
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

Loading…