Iodine → HCID 67781769, compound

HRID 275072Notes

Reaction equation

HRID 275072 reaction equation
[I:1]I.[C:3]([O:6][CH:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C:16](=[CH:17][C:18](=[O:26])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3)(=[O:5])[CH3:4]>C(O)(=O)C>[C:3]([O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C:16](=[CH:17][C:18](=[O:26])[CH:19]([I:1])[CH2:20]1)[CH2:15][CH2:14]3)(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 807IodineHCID 12497354HCID 12497354, compound

Product 1

HCID 67781769HCID 67781769, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.79 g (11 mmol) of iodine is added to 3.28 g (10 mmol) of 17-acetoxy-androst-4-en-3-one and 0.875 g (11 mmol) of CuO in 30 ml of glacial acetic acid with stirring at room temperature. The reaction solution is stirred under nitrogen atmosphere for 24 hours at 60° C. Under reduced pressure, acetic acid is distilled off, and the residue is taken up in 50 ml of water. The water phase is extracted 3 times with 50 ml of ethyl acetate each, the ethyl acetate phases are washed with sodium thiosulfate solution and dried on sodium sulfate. Concentration by evaporation of the solution yields 4.5 g of crude product. After recrystallization from ethyl acetate, 2.85 g of 17β-acetoxy-2-iodo-androst-4-en-3-one (65% of theory) of melting point 92° C. is obtained.

Workup

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

Sources & evidence

ORD record
ord-9bb4211f3a004d0e8ee152ae9dbd6e06
Source dataset
uspto-grants-1995_02
Patent number
US05391778

Reaction notes

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