HCID 86738326, compound → HCID 53632533, compound

HRID 2059305Notes

Reaction equation

HRID 2059305 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)[CH:11]=[CH:10][C:9]1=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]2)[C:2]#[CH:3]>O1CCOCC1>[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])[CH:6]=[CH:5]2)[C:2]#[CH:3]

Participants

3

Reactant 1

HCID 86738326HCID 86738326, compound

Product 1

HCID 53632533HCID 53632533, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 190 mg of 10-(2-propynyl)estra-4,6-diene-3,17-dione, 168 mg of dichlorodicyanoquinone and 10 ml of dioxane is heated at reflux for 5 hours. The mixture is cooled and filtered and the filtrate is diluted with ether, washed with aqueous 1 N sodium hydroxide solution and brine, dried and then concentrated. The resulting residue is chromatographed on silica gel using 50% ethyl acetate/hexane to give 10-(2-propynyl)estra-1,4,6-triene-3,17-dione. This compound melts at about 185°-189° C. after recrystallization from ethyl acetate/hexane and it has the following structural formula ##STR12##

Workup

  1. temperatureis heated
  2. temperatureat reflux for 5 hours
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. additionthe filtrate is diluted with ether
  6. washwashed with aqueous 1 N sodium hydroxide solution and brine
  7. customdried
  8. concentrationconcentrated
  9. customThe resulting residue is chromatographed on silica gel using 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-5a57074246b84011aebe45abc98e836a
Source dataset
uspto-grants-1982_03
Patent number
US04322416

Reaction notes

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