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

HRID 371847Notes

Reaction equation

HRID 371847 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 together for a period of 1 hour. On cooling 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. additionis added
  2. filtrationthe suspension filtered
  3. customThe residue is chromatographed on silica gel
  4. washeluted with methylenechloride
  5. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-f9f0e164010b422faa5463e3619c012f
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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