2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86734727, compound

HRID 2397963Notes

Reaction equation

HRID 2397963 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][CH3:3].[C:6]([OH:10])(=[O:9])[CH2:7][CH3:8].[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27][OH:28])[C:21](=[CH:22][C:23](=[O:32])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[C:1]([OH:5])(=[O:4])[CH2:2][CH3:3].[C:6]([OH:10])(=[O:9])[CH2:7][CH3:8].[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27][OH:28])[C:21](=[CH:22][C:23](=[O:32])[CH:24]=[CH:25]1)[CH2:20][CH2:19]3

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86734728HCID 86734728, compound

Product 1

HCID 86734727HCID 86734727, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

17β,19-Dihydroxy-4-androsten-3-one dipropionate and dichlordicyanobenzoquinone are refluxed in anhydrous dioxane for about 48 hours. The mixture is cooled and filtered and the filtrate concentrated under vacuum. Methylenechloride is added and the mixture filtered. The filtrate is washed well with water, dried over sodium sulfate and the solvent removed. Chromatography on silica gel and elution with methylenechloride results in a solid which is crystallized from acetone-hexane to yield the desired 17β,19-dihydroxy-1,4-androstadien-3-one dipropionate.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under vacuum
  4. additionMethylenechloride is added
  5. filtrationthe mixture filtered
  6. washThe filtrate is washed well with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent removed
  9. washChromatography on silica gel and elution with methylenechloride
  10. customresults in a solid which
  11. customis crystallized from acetone-hexane

Sources & evidence

ORD record
ord-398d78a9f1b6451dbfbf2f130a8f6e07
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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