2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 54515806, compound

HRID 440435Notes

Reaction equation

HRID 440435 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][O:10][C:11]2=[O:21])[CH2:3]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH3:13][C@:12]12[CH2:14][CH2:15][C@H:16]3[C@@H:7]([CH:6]=[CH:5][C:4]4[C@:17]3([CH3:20])[CH:18]=[CH:19][C:2](=[O:1])[CH:3]=4)[C@@H:8]1[CH2:9][O:10][C:11]2=[O:21]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 54167320HCID 54167320, compound

Product 1

HCID 54515806HCID 54515806, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 100 mg of 3β-hydroxy-16-oxaandrost-5-en-17-one, 370 mg of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 10 ml of dioxane was refluxed overnight. After completion of the reaction, the insoluble matters were removed by filtration, and the filtrate was flowed into an activated alumina layer and eluted with methylene chloride. The solvent was distilled out, and the resultant crude product was purified by TLC [developing solvent; chloroform: acetone (19:1)] to obtain 48 mg of 16-oxaandrosta-1,4,6-triene-3,17-dione.

Workup

  1. temperaturewas refluxed overnight
  2. customAfter completion of the reaction
  3. customthe insoluble matters were removed by filtration
  4. washeluted with methylene chloride
  5. distillationThe solvent was distilled out
  6. customthe resultant crude product was purified by TLC [developing solvent; chloroform: acetone (19:1)]

Sources & evidence

ORD record
ord-ebe0b411799d46f690d8fef8a063e00e
Source dataset
uspto-grants-1996_05
Patent number
US05519051

Reaction notes

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