21-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione → 21-Bromo-5alpha-pregnane-3,11,20-trione

HRID 1077023노트

반응식

HRID 1077023 반응식
[Br:1][CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Br:1][CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C:13](=[O:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

참가 물질

4

반응물 2

HCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dioneHCID 131709961Jones' reagent

생성물 1

HCID 8673347421-Bromo-5alpha-pregnane-3,11,20-trione수율 85.4%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

21-Bromo-3α-hydroxy-5α-pregnane-11,20-dione (412 mg.) in acetone (20 ml) was stirred during dropwise addition of Jones reagent (0.4 ml) at room temperature. After 10 minutes, the reaction mixture was poured onto water extracted with chloroform and the combined chloroform extract was washed with water, dried (MgSO4) and evaporated. The residue was crystallised from ether/petrol to give title compound (350 mg) as white microcrystals 170°, [α]D + 132° (c 1.1).

후처리

  1. additionthe reaction mixture was poured onto water
  2. extractionextracted with chloroform
  3. extractionthe combined chloroform extract
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was crystallised from ether/petrol

출처 및 근거

ORD 기록
ord-95b781a7d09e4e778756b47f6166412c
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959260

반응 노트

불러오는 중…