2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 18632036, compound

HRID 621625Notes

Reaction equation

HRID 621625 reaction equation
[F:1][C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:24])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:22])[CH2:14][C@H:15]1[CH3:21])[CH2:10][C:9]3=[CH2:23].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[F:1][C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:24])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:22])[CH:14]=[C:15]1[CH3:21])[CH2:10][C:9]3=[CH2:23]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18632035HCID 18632035, compound

Product 1

HCID 18632036HCID 18632036, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The organic layer is washed with sodium bicarbonate solution, dried and evaporated in vacuo. The residue is purified by column chromatography on silica gel thus giving pure 16α-fluoro-1β-methyl-7-methylenandrost-4-ene-3,17-dione (198 mg). 16α-fluoro-1β-methyl-7-methylenandrost-4-ene-3,17-dione (331 mg) and dichlorodicyanobenzoquinone (363 mg) are refluxed in dioxane solution (20 ml) for about 15 hrs. Then the precipitate is filtered off and the filtrate evaporated in vacuo. The residue is taken up in ethyl acetate and the organic solution washed, dried and evaporated in vacuo. The residue is chromatographed on silica gel using hexane/ethyl acetate as eluant to give pure 16α-fluoro-1-methyl-7-methylenandrosta-1,4-diene-3,17-dione (230 mg).

Workup

  1. filtrationThen the precipitate is filtered off
  2. customthe filtrate evaporated in vacuo
  3. washthe organic solution washed
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-7a6bfd08eb6d4900bb4a6ec2de94de22
Source dataset
uspto-grants-1989_04
Patent number
US04824830

Reaction notes

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