Toluene → Androsta-4,16-dien-3-one

HRID 616643

反応式

HRID 616643 の反応式
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH:10]=[CH:11]2)[CH2:3]1.C1(C)C=CC=CC=1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>O>[CH3:13][C@:12]12[CH2:14][CH2:15][C@H:16]3[C@@H:7]([CH2:6][CH2:5][C:4]4[C@:17]3([CH3:20])[CH2:18][CH2:19][C:2](=[O:1])[CH:3]=4)[C@@H:8]1[CH2:9][CH:10]=[CH:11]2

参加物

5

反応物 3

HCID 1140Toluene2 回HCID 11143Aluminum isopropoxideHCID 150900Androsta-5,16-dien-3 beta-ol

生成物 1

HCID 92979Androsta-4,16-dien-3-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

250 ml. of a solution of 68 g. of 3β-hydroxy-androsta5,16-diene in 1.25 l. of toluene and 0.5 l. of cyclohexanone was distilled to obtain an anhydrous solution. A solution of 34 g. of aluminum isopropoxide in 170 ml. of dry toluene was added. The mixture was slowly distilled during 30 minutes to remove the acetone formed. After completion of the reaction water was added, and the mixture steam distilled to remove volatile components. the residue was extracted with methyl isobutyl ketone and the extract washed with an aqueous hydrogen chloride solution and water. The solvent was removed by distillation in vacuo and the residue was crystallized from acetone; 38.1 g. of androsta-4,16-dien-3-one were obtained. Recyrstallization from acetone yielded a pure product melting at a 131°-133° C. mol. peak in mass spectrum (m/e): 270. EXAMPLE IV

後処理

  1. distillationof cyclohexanone was distilled
  2. customto obtain an anhydrous solution
  3. distillationThe mixture was slowly distilled during 30 minutes
  4. customto remove the acetone
  5. customformed
  6. additionwas added
  7. distillationthe mixture steam distilled
  8. customto remove volatile components
  9. extractionthe residue was extracted with methyl isobutyl ketone
  10. washthe extract washed with an aqueous hydrogen chloride solution and water
  11. customThe solvent was removed by distillation in vacuo
  12. customthe residue was crystallized from acetone

出典と根拠

ORDレコード
ord-02ef52138c634f3c8b2ec277be9d0e1f
出典データセット
uspto-grants-1978_02
特許番号
US04075233

関連ノート

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