Water → 3-Oxo-17beta(1oxopropoxy)androst-4en-19-al

HRID 1678957Notes

Reaction equation

HRID 1678957 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C@@H:15]([O:21][C:22](=[O:25])[CH2:23][CH3:24])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:26])[CH2:5][CH2:4]2.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[O:26]=[C:6]1[CH2:5][CH2:4][C@@:3]2([CH:2]=[O:1])[C:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[O:21][C:22](=[O:25])[CH2:23][CH3:24])=[CH:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 5422328719-Hydroxy-17beta(1-oxopropoxy)androst-4-en-3-oneHCID 131709961Jones' reagent

Product 1

HCID 867345753-Oxo-17beta(1oxopropoxy)androst-4en-19-al

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 14 g of 19-hydroxy-17β-(1-oxopropoxy)androst-4-en-3-one in 1 liter of acetone cooled in an ice bath is added 13.3. ml of Jones reagent over 1 hour after which the reaction mixture is poured into a large volume of water and extracted with ether. The ether extract is dried over magnesium sulfate, filtered and the solvent removed. The residue is crystallized from acetone-hexane to give 3-oxo-17β(1-oxopropoxy)-androst-4-en-19-al, M.P. 119°-121° C.

Workup

  1. additionis added 13.3
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. dry with materialis dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe residue is crystallized from acetone-hexane

Sources & evidence

ORD record
ord-2dc0fb2caf424bf7a781d1ba9d0a4003
Source dataset
uspto-grants-1978_03
Patent number
US04078060

Reaction notes

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