Chloranil → HCID 86734740, compound

HRID 1834941Notes

Reaction equation

HRID 1834941 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[OH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]2[C@H:16]3[C@H:27]([CH2:28][CH2:29][C@:11]12[CH3:12])[C@:24]1([CH2:25][OH:26])[C:19](=[CH:20][C:21](=[O:30])[CH2:22][CH2:23]1)[CH2:18][CH2:17]3.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(O)(C)(C)C>[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[OH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]2[C@H:16]3[C@H:27]([CH2:28][CH2:29][C@:11]12[CH3:12])[C@:24]1([CH2:25][OH:26])[C:19](=[CH:20][C:21](=[O:30])[CH2:22][CH2:23]1)[CH:18]=[CH:17]3

Participants

4

Reactant 2

HCID 8371ChloranilHCID 86734741HCID 86734741, compound

Product 1

HCID 86734740HCID 86734740, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

17β,19-Dihydroxy-4-androsten-3-one diacetate and chloranil are dissolved in t-butanol which is rapidly brought to reflux. The t-butanol is distilled at atmospheric pressure at such a rate that the total reflux and distillation time equals one hour. The dark residue which remains is triturated with hot chloroform and filtered. The filtrate is extracted with water, a 2% sodium hydroxide solution and again with water. The organic layer is dried over magnesium sulfate and the solvent removed to yield 17β,19-dihydroxy-4,6-androstadien-3-one diacetate. The diene so prepared is refluxed with dichlorodicyanobenzoquinone in anhydrous dioxane for a period of about 48 hours. The mixture is cooled, filtered and the filtrate poured onto a mixture of methylenechloride and water. The organic layer is separated, washed with water, dried well over magnesium sulfate and the solvent removed. The dark residue remaining is chromatographed on silica gel and eluted with methylenechloride to yield from the eluate the desired 17β,19-dihydroxy-1,4,6-androstatrien-3-one diacetate.

Workup

  1. temperatureto reflux
  2. distillationThe t-butanol is distilled at atmospheric pressure at such a rate that the
  3. temperaturetotal reflux
  4. distillationdistillation time equals one hour
  5. customThe dark residue which remains is triturated with hot chloroform
  6. filtrationfiltered
  7. extractionThe filtrate is extracted with water
  8. dry with materialThe organic layer is dried over magnesium sulfate
  9. customthe solvent removed

Sources & evidence

ORD record
ord-13aec762a8f54a0bb5c259c432f100c1
Source dataset
uspto-grants-1978_01
Patent number
US04071624

Reaction notes

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