Iodine → 2-Iodo-1alpha-methyl-androst-4-ene-3,17-dione

HRID 275066Notes

Reaction equation

HRID 275066 reaction equation
[I:1]I.[CH3:3][C@@H:4]1[C@@:21]2([CH3:22])[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:15]2=[O:23])=[CH:7][C:6](=[O:24])[CH2:5]1>C(O)(=O)C>[I:1][CH:5]1[C@H:4]([CH3:3])[C@@:21]2([CH3:22])[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:15]2=[O:23])=[CH:7][C:6]1=[O:24]

Participants

4

Reactant 2

HCID 807IodineHCID 109575614-Androstene-3,17-dione, 1alpha-methyl-

Product 1

HCID 677814542-Iodo-1alpha-methyl-androst-4-ene-3,17-dioneYield 106.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.3 g (40 mmol) of iodine is added to 10 g (33 mmol) of 1α-methyl-androst-4-ene-3,17-dione and 7.33 g (40 mmol) of CuO in 300 ml of glacial acetic acid with stirring at room temperature. It is stirred under nitrogen atmosphere for 24 hours at 60° C. Under reduced pressure, acetic acid is distilled off. The residue is added in 600 ml of water, the product is extracted 3 times with 200 ml of ethyl acetate each, the combined ethyl acetate phases are washed neutral with sodium thiosulfate solution, then with saturated sodium carbonate solution and dried on sodium sulfate. After concentration by evaporation of the solution and drying of the substance at 0.8 torr, 15.0 g (106% of theory) of 2-iodo-1α-methyl-androst-4-ene-3,17-dione is obtained as crude product.

Workup

  1. stirringIt is stirred under nitrogen atmosphere for 24 hours at 60° C
  2. distillationUnder reduced pressure, acetic acid is distilled off
  3. additionThe residue is added in 600 ml of water
  4. extractionthe product is extracted 3 times with 200 ml of ethyl acetate each, the combined ethyl acetate phases
  5. washare washed neutral with sodium thiosulfate solution
  6. dry with materialwith saturated sodium carbonate solution and dried on sodium sulfate
  7. concentrationAfter concentration
  8. customby evaporation of the solution
  9. customdrying of the substance at 0.8 torr

Sources & evidence

ORD record
ord-8616060267af44159b0943e2bceaec50
Source dataset
uspto-grants-1995_02
Patent number
US05391778

Reaction notes

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