2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 18632042, compound

HRID 621620Notes

Reaction equation

HRID 621620 reaction equation
[CH3:1][C@H:2]1[C@@:19]2([CH3:20])[C:6]([C:7](=[CH2:24])[C@@H:8]([CH3:23])[C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][C@@H:12]([F:22])[C:13]2=[O:21])=[CH:5][C:4](=[O:25])[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]([C:7](=[CH2:24])[C@@H:8]([CH3:23])[C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][C@@H:12]([F:22])[C:13]2=[O:21])=[CH:5][C:4](=[O:25])[CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18632034HCID 18632034, compound

Product 1

HCID 18632042HCID 18632042, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.560 g of 1β,7α-dimethyl-16α-fluoro-6-methylenandrost-4-ene-3,17-dione and 0.59 g of dichlorodicyanobenzoquinone is refluxed in 20 ml of anhydrous dioxane for about 15 hrs. The the reaction mixture is filtered, the solvent removed in vacuo, the residue dissolved in ethyl acetate, the organic layer washed with water, dried over sodium sulfate and the solvent evaporated under vacuum. The crude product is chromatographed on silica gel using hexane/ethyl acetate 40% as eluant to yield 0.42 g of pure 1,7α-dimethyl-16α-fluoro-6-methylenandrosta-1,4-diene-3,17-dione.

Workup

  1. filtrationThe the reaction mixture is filtered
  2. customthe solvent removed in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washthe organic layer washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent evaporated under vacuum
  7. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-3541f636ea634e97984adc70e2e1db23
Source dataset
uspto-grants-1989_04
Patent number
US04824830

Reaction notes

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