2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13371253, compound

HRID 280836Notes

Reaction equation

HRID 280836 reaction equation
[CH3:1][C@@H:2]1[C@@:19]2([CH3:20])[C:6]([CH2:7][C@@H:8]([CH3:22])[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:23])[CH2:3]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH3:1][C:2]1[C@@:19]2([CH3:20])[C:6]([CH2:7][C@@H:8]([CH3:22])[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:23])[CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 53793753HCID 53793753, compound

Product 1

HCID 13371253HCID 13371253, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

30 g of 1α,7α-dimethyl-4-androstene-3,17-dione is heated under reflux in 700 ml of dioxane with 30 g of dichlorodicyanobenzoquinone for 8 hours. After cooling, the product is suctioned off from undissolved matter, washed with dioxane, and the filtrate concentrated under vacuum. The residue is chromatographed on silica gel and recrystallized from acetone/hexane, thus obtaining 18 g of 1,7α-dimethylandrosta-1,4-diene-3,17-dione, mp 148°-151° C.

Workup

  1. temperatureAfter cooling
  2. washwashed with dioxane
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe residue is chromatographed on silica gel
  5. customrecrystallized from acetone/hexane

Sources & evidence

ORD record
ord-638630e9283d4febbc3b9eb16dc99dfc
Source dataset
uspto-grants-1986_05
Patent number
US04591585

Reaction notes

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