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

HRID 275068

반응식

HRID 275068 반응식
[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]

참가 물질

4

반응물 2

HCID 807IodineHCID 6128Androstenedione

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-990b6e3dace445888a15951656429e7f
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391778

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