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

HRID 275068

Reaction equation

HRID 275068 reaction equation
[I:1]I.[CH3:3][C@:4]12[CH2:21][CH2:20][C@H:19]3[C@@H:9]([CH2:10][CH2:11][C:12]4[C@:17]3([CH3:18])[CH2:16][CH2:15][C:14](=[O:22])[CH:13]=4)[C@@H:8]1[CH2:7][CH2:6][C:5]2=[O:23]>C(O)(=O)C>[I:1][CH:15]1[CH2:16][C@@:17]2([CH3:18])[C:12]([CH2:11][CH2:10][C@@H:9]3[C@@H:19]2[CH2:20][CH2:21][C@@:4]2([CH3:3])[C@H:8]3[CH2:7][CH2:6][C:5]2=[O:23])=[CH:13][C:14]1=[O:22]

Participants

4

Reactant 2

HCID 807IodineHCID 6128Androstenedione

Product 1

HCID 545692722-Iodo-androst-4-ene-3,17-dioneYield 109.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.79 g (11 mmol) of iodine is added to 2.86 g (10 mmol) of androst-4-ene-3,17-dione and 0.875 g (11 mmol) of CuO in 30 ml of glacial acetic acid with stirring at room temperature. The reaction mixture is stirred under nitrogen atmosphere for 24 hours at 60° C. Under reduced pressure, acetic acid is distilled off and the residue is mixed with 50 ml of water. The water phase is extracted 3 times with 50 ml of ethyl acetate each, the combined ethyl acetate phases are washed with sodium thiosulfate solution and dried on sodium sulfate. After concentration by evaporation of the solution, 4.5 g of crude product is obtained. After recrystallization from ethyl acetate, 2.9 g of 2-iodo-androst-4-ene-3,17-dione (70% of theory) of melting point 92° C. is obtained.

Workup

  1. stirringThe reaction mixture is stirred under nitrogen atmosphere for 24 hours at 60° C
  2. distillationUnder reduced pressure, acetic acid is distilled off
  3. additionthe residue is mixed with 50 ml of water
  4. extractionThe water phase is extracted 3 times with 50 ml of ethyl acetate each, the combined ethyl acetate phases
  5. washare washed with sodium thiosulfate solution
  6. customdried on sodium sulfate
  7. concentrationAfter concentration
  8. customby evaporation of the solution

Sources & evidence

ORD record
ord-990b6e3dace445888a15951656429e7f
Source dataset
uspto-grants-1995_02
Patent number
US05391778

Linked notes

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