Chloranil → HCID 86738326, compound

HRID 2059306Notes

Reaction equation

HRID 2059306 reaction equation
[CH2:1]([C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]1=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]2)[C:2]#[CH:3].C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(O)(C)(C)C.C(OCC)(=O)C>[CH2:1]([C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]4)[CH:11]=[CH:10][C:9]1=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]2)[C:2]#[CH:3]

Participants

5

Reactant 2

HCID 8371ChloranilHCID 9904788Plomestane

Product 1

HCID 86738326HCID 86738326, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 250 mg of 10-(2-propynyl)estr-4-ene-3,17-dione, and 460 mg of chloranil in 17 ml of tert-butyl alcohol is heated at reflux temperature for 3 hours. The mixture is diluted with ethyl acetate and filtered and the filtrate is washed with aqueous 1 N sodium hydroxide and with brine, and dried. The solvent is then evaporated and the residue is chromatographed on silica gel using ethyl acetate-hexane to give 10-(2-propynyl)estra-4,6-diene-3,17-dione. This compound has the following structural formula ##STR13##

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3 hours
  3. filtrationfiltered
  4. washthe filtrate is washed with aqueous 1 N sodium hydroxide and with brine
  5. customdried
  6. customThe solvent is then evaporated
  7. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-f08ce9da20994567bce7e8afb0d19547
Source dataset
uspto-grants-1982_03
Patent number
US04322416

Reaction notes

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