Plomestane → HCID 86738325, compound

HRID 2059304Notes

Reaction equation

HRID 2059304 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]>O1CCOCC1.CCOCC>[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])[CH:6]=[CH:5]2)[C:2]#[CH:3]

Participants

4

Reactant 1

HCID 9904788Plomestane

Product 1

HCID 86738325HCID 86738325, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 150 mg of 10-(2-propynyl)-estr-4-ene-3,17-dione, and 300 mg of dichlorodicyanoquinone in 10 ml of dioxane is refluxed for 20 hours. The mixture is cooled and diluted with ether and then washed with aqueous sodium carbonate and dried. The solvent is evaporated and the residue is chromatographed on silica gel in ethyl acetate/hexane to give 10-(2-propynyl)-estra-1,4-diene-3,17-dione melting at about 200°-201° C. This compound has the following structural formula ##STR11##

Workup

  1. temperatureis refluxed for 20 hours
  2. temperatureThe mixture is cooled
  3. washwashed with aqueous sodium carbonate
  4. customdried
  5. customThe solvent is evaporated
  6. customthe residue is chromatographed on silica gel in ethyl acetate/hexane

Sources & evidence

ORD record
ord-4826164723a24b618e15a576aa0fbd0e
Source dataset
uspto-grants-1982_03
Patent number
US04322416

Reaction notes

Loading…