Chloranil → HCID 54166859, compound

HRID 1382733Notes

Reaction equation

HRID 1382733 reaction equation
[Br:1][C:2]#[C:3][CH2:4][C@@:5]12[C@@H:22]3[C@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C:17](=[O:23])[CH2:16][CH2:15]4)[CH2:12][CH2:11][C:10]1=[CH:9][C:8](=[O:24])[CH2:7][CH2:6]2.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(O)(C)(C)C.C(OCC)(=O)C>[Br:1][C:2]#[C:3][CH2:4][C@@:5]12[C@@H:22]3[C@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C:17](=[O:23])[CH2:16][CH2:15]4)[CH:12]=[CH:11][C:10]1=[CH:9][C:8](=[O:24])[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 8371ChloranilHCID 14209731HCID 14209731, compound

Product 1

HCID 54166859HCID 54166859, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 313 mg of 10β-(3-bromo-2-propynyl)estr-4-ene-3,17-dione and 575 mg of chloranil in 21 ml of tert-butyl alcohol is heated at reflux for 2 hours. The mixture is diluted with ethyl acetate and filtered and the filtrate is washed with aqueous 1N sodium hydroxide, with brine and dried over sodium sulphate. The solvent is then evaporated and the residue chromatographed on silica gel using ethylacetate/n-hexane to give 140 mg of the title compound.

Workup

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

Sources & evidence

ORD record
ord-8edba0c527c64ecf8ba8fea3fa74dde0
Source dataset
uspto-grants-1989_02
Patent number
US04808578

Reaction notes

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