Iodine → 17beta-Acetoxy-2-iodo-1alpha-methyl-androst-4-en-3-one

HRID 275070ノート

反応式

HRID 275070 の反応式
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:25])[CH2:17][C@@H:18]1[CH3:24])[CH2:13][CH2:12]3)(=[O:3])[CH3:2].[I:26]I>C(O)(=O)C>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:25])[CH:17]([I:26])[C@@H:18]1[CH3:24])[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 807IodineHCID 2130949917beta-Acetoxy-1alpha-methyl-androst-4-en-3-one

生成物 1

HCID 6778185217beta-Acetoxy-2-iodo-1alpha-methyl-androst-4-en-3-one収率 93.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
60 °C

実験手順

6.88 g (20 mmol) of 17β-acetoxy-1α-methyl-androst-4-en-3-one and 1.75 g (22 mmol) of CuO in 60 ml of acetic acid are mixed with stirring at room temperature with 5.58 g (22 mmol) of iodine and stirred under nitrogen atmosphere for 24 hours at 60° C. Under reduced pressure, the acetic acid is largely distilled off and the residue is taken up in 100 ml of water. The water phase is extracted 3 times with 100 ml of ethyl acetate each. The ethyl acetate phases are washed with sodium thiosulfate solution and dried on sodium sulfate. After concentration by evaporation of the solution, 10 g of crude product is obtained. Recrystallization from ethyl acetate yields 8.8 g of 17β-acetoxy-2-iodo-1α-methyl-androst-4-en-3-one (93% of theory) of melting point 102° C.

後処理

  1. distillationUnder reduced pressure, the acetic acid is largely distilled off
  2. extractionThe water phase is extracted 3 times with 100 ml of ethyl acetate each
  3. washThe ethyl acetate phases are washed with sodium thiosulfate solution
  4. customdried on sodium sulfate
  5. concentrationAfter concentration
  6. customby evaporation of the solution
  7. custom10 g of crude product is obtained
  8. customRecrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-4888f098901b4f7f97854089f232c0f4
出典データセット
uspto-grants-1995_02
特許番号
US05391778

反応ノート

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