Toluene → HCID 86740367, compound

HRID 464153Notes

Reaction equation

HRID 464153 reaction equation
C([C@@]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9]C1=CC(=O)CC2)C.[C:23]1(Cl)C(=O)C(Cl)=C(Cl)C(=O)[C:24]=1Cl.[C:35]1([CH3:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH2:41]=[C:35]1[CH2:40][CH2:39][C@@:38]2([CH2:23][CH3:24])[C:37]([CH:9]=[CH:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[O:21])=[CH:36]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 8371ChloranilHCID 1859950110beta-Ethyl-estra-4-ene-3,17-dione

Product 1

HCID 86740367HCID 86740367, compound

Procedure

290 mg of 10β-ethyl-estra-4-ene-3,17-dione and 594 mg of chloranil are taken up in 15 ml of toluene. The mixture is refluxed for 20 hours in an atmosphere of nitrogen. The solvent is washed with several small portions of 5% sodium hydroxide and then with water. It is dried over anhydrous sodium sulfate for several hours. The solution is filtered and the solvent removed under vacuum. The amorphous solid obtained is triturated with ether, filtered and purified by chromatography over silica gel using a n-hexane-ethyl acetate solvent.

Workup

  1. temperatureThe mixture is refluxed for 20 hours in an atmosphere of nitrogen
  2. washThe solvent is washed with several small portions of 5% sodium hydroxide
  3. dry with materialIt is dried over anhydrous sodium sulfate for several hours
  4. filtrationThe solution is filtered
  5. customthe solvent removed under vacuum
  6. customThe amorphous solid obtained
  7. customis triturated with ether
  8. filtrationfiltered
  9. custompurified by chromatography over silica gel using a n-hexane-ethyl acetate solvent

Sources & evidence

ORD record
ord-c5a9462c548345a4b9e29d8527ecbb80
Source dataset
uspto-grants-1985_10
Patent number
US04546098

Reaction notes

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