HCID 7060880, compound → HCID 86736324, compound

HRID 1390783Notes

Reaction equation

HRID 1390783 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH2:20][OH:21])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:22])[CH2:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:13][C@:12]12[CH2:14][CH2:15][C@H:16]3[C@@H:7]([CH2:6][CH:5]=[C:4]4[C@:17]3([CH:20]=[O:21])[CH2:18][CH2:19][C:2](=[O:1])[CH2:3]4)[C@@H:8]1[CH2:9][CH2:10][C:11]2=[O:22]

Participants

4

Reactant 2

HCID 7060880HCID 7060880, compoundHCID 131709961Jones' reagent

Product 1

HCID 86736324HCID 86736324, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3β,19-dihydroxy-5-androsten-17-one in acetone at 10° C. is added two equivalents of Jones Reagent with stirring. After an additional 15 minutes the upper acetone layer is decanted and poured onto ice water. The precipitate which forms is filtered, washed with water and dissolved in ether. The ether solution is dried over magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue from an acetone-hexane solution yields 5-androstene-3,17,19-trione.

Workup

  1. customAfter an additional 15 minutes the upper acetone layer is decanted
  2. additionpoured onto ice water
  3. filtrationThe precipitate which forms is filtered
  4. washwashed with water
  5. dissolutiondissolved in ether
  6. dry with materialThe ether solution is dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customCrystallization of the residue from an acetone-hexane solution

Sources & evidence

ORD record
ord-2e57862597534487b42c416011717cc4
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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