Chloranil → HCID 53714059, compound

HRID 440436Notes

Reaction equation

HRID 440436 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][O:4][C:3]2=[O:21].ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(O)(C)(C)C>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH:8]=[CH:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][O:4][C:3]2=[O:21]

Participants

4

Reactant 2

HCID 8371ChloranilHCID 67684012HCID 67684012, compound

Product 1

HCID 53714059HCID 53714059, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

415 mg of 16-oxaandrost-4-ene-3,17-dione, 768 mg of 2,3,5,6-tetrachloro-1,4-benzoquinone and 30 ml of t-butanol were refluxed overnight. The insoluble matters were removed from the reaction mixture, the solvent was distilled out, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium bicarbonate solution, water and saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was distilled out, and the resultant crude product was purified by TLC [developing solvent; chloroform: acetone (39:1)) to obtain 220 mg of 16-oxaandrosta-4,6-diene-3,17-dione.

Workup

  1. customThe insoluble matters were removed from the reaction mixture
  2. distillationthe solvent was distilled out
  3. additionwater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with 5% aqueous sodium bicarbonate solution, water and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled out
  8. customthe resultant crude product was purified by TLC [

Sources & evidence

ORD record
ord-88134ea0e8d343bfaf25a2545fd9bed6
Source dataset
uspto-grants-1996_05
Patent number
US05519051

Reaction notes

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