Chloranil → 19-Hydroxy-4,6-androstadiene-3,17-dione

HRID 371851

반응식

HRID 371851 반응식
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(O)(C)(C)C>[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH:10]=[CH:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2

참가 물질

4

반응물 2

HCID 8371ChloranilHCID 25237919-Hydroxyandrostenedione

생성물 1

HCID 5428584419-Hydroxy-4,6-androstadiene-3,17-dione

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

19-Hydroxy-4-androstene-3,17-dione and chloranil are dissolved in t-butanol and rapidly brought to reflux. The t-butanol is removed by distillation at atmospheric pressure at such a rate so that the total reflux and distillation time equals one hour. The dark pasty residue is triturated with hot chloroform and cooled. The solid which remains is removed by filtration and the filtrate successively extracted with water, a 2% sodium hydroxide solution and again with water. The organic layer is dried over magnesium sulfate and the solvent removed under vacuum to yield 19-hydroxy-4,6-androstadiene-3,17-dione. The diene so prepared is dissolved in acetone and chilled in an ice bath. Jones reagent is added over a period of about 10 minutes and stirring continued for an additional 45 minutes. The mixture is poured onto water. The solid which forms is filtered and recrystallized from benzene to yield 4,6-androstadiene-3,17,19-trione.

후처리

  1. temperatureto reflux
  2. customThe t-butanol is removed by distillation at atmospheric pressure at such a rate so that the
  3. temperaturetotal reflux
  4. distillationdistillation time equals one hour
  5. customThe dark pasty residue is triturated with hot chloroform
  6. temperaturecooled
  7. customThe solid which remains is removed by filtration
  8. extractionthe filtrate successively extracted with water
  9. dry with materialThe organic layer is dried over magnesium sulfate
  10. customthe solvent removed under vacuum

출처 및 근거

ORD 기록
ord-2d625556eb3e4ec295d382f39f9457ff
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04087524

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