Sodium Carbonate → 19-Hydroxy-17beta(1-oxopropoxy)androst-4-en-3-one

HRID 597357

Reaction equation

HRID 597357 reaction equation
[O:1]=[C:2]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:27]([CH2:28][CH2:29][C@:7]12[CH3:8])[C@:20]1([CH2:21][O:22]C(=O)CC)[C:15](=[CH:16][C:17](=[O:30])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)[CH2:3][CH3:4].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[OH:22][CH2:21][C@@:20]12[C@@H:27]3[C@H:12]([C@H:9]4[C@@:7]([CH2:29][CH2:28]3)([CH3:8])[C@@H:6]([O:5][C:2](=[O:1])[CH2:3][CH3:4])[CH2:11][CH2:10]4)[CH2:13][CH2:14][C:15]1=[CH:16][C:17](=[O:30])[CH2:18][CH2:19]2

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 5434261217beta,19-Bis(1-oxopropoxy)-androst-4-en-3-one

Product 1

HCID 5422328719-Hydroxy-17beta(1-oxopropoxy)androst-4-en-3-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 11 g of 17β,19-bis(1-oxopropoxy)androst-4-en-3-one in 2 liters of methanol is treated with 2.5 g of sodium carbonate in 250 ml of water and refluxed for one hour after which the reaction mixture is poured into 10 liters of water, and the solid collected by filtration. The solid is dissolved in methylene chloride, dried over magnesium sulfate, filtered and the solvent removed. The residue is crystallized from acetone-hexane yielding 6 g of 19-hydroxy-17β(1-oxopropoxy)androst-4-en-3-one. M.P. 160°-162° C.

Workup

  1. temperaturerefluxed for one hour after which the reaction mixture
  2. filtrationthe solid collected by filtration
  3. dissolutionThe solid is dissolved in methylene chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe residue is crystallized from acetone-hexane yielding 6 g of 19-hydroxy-17β(1-oxopropoxy)androst-4-en-3-one

Sources & evidence

ORD record
ord-a7ea5910cdac4fe9a60d62136b886b9d
Source dataset
uspto-grants-1977_03
Patent number
US04013762

Linked notes

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