Toluene → Androsta-4,16-dien-3-one

HRID 616643

반응식

HRID 616643 반응식
[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

참가 물질

5

반응물 3

HCID 1140Toluene2회HCID 11143Aluminum isopropoxideHCID 150900Androsta-5,16-dien-3 beta-ol

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-02ef52138c634f3c8b2ec277be9d0e1f
출처 데이터셋
uspto-grants-1978_02
특허 번호
US04075233

연결된 노트

불러오는 중…