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

HRID 1390729Notes

Reaction equation

HRID 1390729 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 dichlorodicyanobenzoquinone are refluxed in anhydrous dioxane for a period of 48 hours. The mixture is cooled and filtered and the filtrate concentrated under vacuum. Methylenechloride is added and the resulting mixture filtered. The filtrate is washed well with water, dried over sodium sulfate and the solvent removed. Chromatography of the residue on silica gel and elution with methylenechloride provides a solid which is crystallized from an acetone-hexane solution 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 resulting mixture filtered
  6. washThe filtrate is washed well with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent removed
  9. washChromatography of the residue on silica gel and elution with methylenechloride
  10. customprovides a solid which
  11. customis crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-569fc9abff5b4abe97f4e089ed2f555e
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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