Potassium Bicarbonate → HCID 70605278, compound

HRID 1390728Notes

Reaction equation

HRID 1390728 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[OH:28])[CH2:6]1)(=O)C.C(=O)(O)[O-].[K+]>CO>[C:25]([O:24][CH2:23][C@@:20]12[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([OH:28])[CH2:13][CH2:12]4)[CH2:9][CH:8]=[C:7]1[CH2:6][C@@H:5]([OH:4])[CH2:22][CH2:21]2)(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 516893Potassium BicarbonateHCID 22806870HCID 22806870, compound

Product 1

HCID 70605278HCID 70605278, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-androstene-3β,17β,19-triol 3,19-diacetate in methanol is added one equivalent of an aqueous 2% solution of potassium bicarbonate. The mixture is heated at its reflux temperature for a period of about 2 hours, concentrated to a small volume under reduced pressure and ether added thereto. The ethereal solution is separated, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue so obtained is crystallized from an acetone-hexane solution to furnish the desired 5-androstene-3β,17β,19-triol 19-acetate.

Workup

  1. temperatureThe mixture is heated at its
  2. temperaturereflux temperature for a period of about 2 hours
  3. concentrationconcentrated to a small volume under reduced pressure and ether
  4. additionadded
  5. customThe ethereal solution is separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue so obtained
  10. customis crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-2ecea15ce482473babb7d6baaaff78ac
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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