Dichloromethane → HCID 15838717, compound

HRID 361317Notes

Reaction equation

HRID 361317 reaction equation
[CH2:1]([C@H:4]1[C:21]2[C@:16]([CH3:23])([CH2:17][CH2:18][C:19](=[O:22])[CH:20]=2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:24])[CH2:9][CH2:8]3)[CH2:5]1)[C:2]#[CH:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.ClCCl>O1CCOCC1>[CH2:1]([C@H:4]1[C:21]2[C@:16]([CH3:23])([CH:17]=[CH:18][C:19](=[O:22])[CH:20]=2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:24])[CH2:9][CH2:8]3)[CH2:5]1)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 9797346HCID 9797346, compound

Product 1

HCID 15838717HCID 15838717, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6β-propargyl-4-androstene-3,17-dione (1) (160 mg, 0.5 mmol) in dry dioxane (30 mL) was added dichlorodicyanobenzoquinone (DDQ, 150 mg, 0.6 mmol), and the reaction mixture was refluxed with stirring for 6 hours. Dilution with 30 mL dichloromethane followed by washing (1% NaOH, water), drying and evaporation in vacuo, gave 125 mg of crude product. The residue was purified by chromatography over silica gel and the product was recrystallized from acetone/hexane to give 95 mg (60% yield) of the title compound (12).

Workup

  1. temperaturethe reaction mixture was refluxed
  2. washby washing (1% NaOH, water)
  3. customdrying
  4. customevaporation in vacuo
  5. customgave 125 mg of crude product
  6. customThe residue was purified by chromatography over silica gel
  7. customthe product was recrystallized from acetone/hexane

Sources & evidence

ORD record
ord-bd56936b938544c08bf539344006e9a4
Source dataset
uspto-grants-1999_02
Patent number
US05866558

Reaction notes

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