Acetic Acid → 19-Hydroxy-1beta-methyl-4-androsten-3,17-dione

HRID 1390740Notes

Reaction equation

HRID 1390740 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[C@H:5]1[CH2:23][C@@H:4]21.C(O)(=O)C>[Zn].C1C=CC=CC=1>[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][C@H:4]2[CH3:23]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 7060589619-Hydroxy-1beta,2beta-methylene-4-androstene-3,17-dione

Product 1

HCID 5427936919-Hydroxy-1beta-methyl-4-androsten-3,17-dione

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

19-Hydroxy-1β,2β-methylene-4-androstene-3,17-dione, zinc powder, and acetic acid are heated to their reflux temperature for a period of about 1 hour. Upon cooling of the reaction mixture, benzene is added and the resulting suspension filtered. The filtrate is evaporated to dryness under vacuum and the residue remaining is chromatographed on a silica gel column and eluted with methylenechloride. The eluate is evaporated to dryness and the residue is crystallized from an acetone-hexane solution to yield 19-hydroxy-1β-methyl-4-androstene-3,17-dione.

Workup

  1. temperaturereflux temperature for a period of about 1 hour
  2. additionis added
  3. filtrationthe resulting suspension filtered
  4. customThe filtrate is evaporated to dryness under vacuum
  5. customthe residue remaining is chromatographed on a silica gel column
  6. washeluted with methylenechloride
  7. customThe eluate is evaporated to dryness
  8. customthe residue is crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-376c085165d049d2a0d17e559e071a53
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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