HCID 14209731, compound → HCID 14209735, compound

HRID 1382732Notes

Reaction equation

HRID 1382732 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>O1CCOCC1.C(OCC)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)[CH2:12][CH2:11][C:10]1=[CH:9][C:8](=[O:24])[CH:7]=[CH:6]2

Participants

4

Reactant 1

HCID 14209731HCID 14209731, compound

Product 1

HCID 14209735HCID 14209735, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 188 mg of 10β-(3-bromo-2-propynyl)estr-4-ene-3,17-dione and 376 mg of dichlorodicyanoquinone in 12.5 ml of dioxane is refluxed for 20 hours. The mixture is cooled and diluted with diethyl ether, then washed with aqueous sodium carbonate solution and dried. The solvent is evaporated and the residue is purified by flash chromatography on silica gel eluting with ethyl acetate:n-hexane 30:70 to give the title compound.

Workup

  1. temperatureis refluxed for 20 hours
  2. temperatureThe mixture is cooled
  3. washwashed with aqueous sodium carbonate solution
  4. customdried
  5. customThe solvent is evaporated
  6. customthe residue is purified by flash chromatography on silica gel eluting with ethyl acetate:n-hexane 30:70

Sources & evidence

ORD record
ord-0ec15d33bbc44031b724d1b08a109a05
Source dataset
uspto-grants-1989_02
Patent number
US04808578

Reaction notes

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