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

HRID 1834977Notes

Reaction equation

HRID 1834977 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

A mixture of 1β,2β-methylene-4-androstene-3,17-dione, zinc powder, and acetic acid is refluxed for one hour. Benzene is added and the suspension filtered. The filtrate is taken to dryness under vacuum. The residue which remains is chromatographed on silica gel and eluted with methylenechloride. Recrystallization of the residue obtained from the eluate from an acetone-hexane solution yields 1β-methyl-4-androstene-3,17-dione.

Workup

  1. temperatureis refluxed for one hour
  2. filtrationthe suspension filtered
  3. customThe residue which remains is chromatographed on silica gel
  4. washeluted with methylenechloride
  5. customRecrystallization of the residue
  6. customobtained from the eluate from an acetone-hexane solution

Sources & evidence

ORD record
ord-d364e8728dfd4f8da80507beca84897a
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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