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

HRID 1576793노트

반응식

HRID 1576793 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 mp 170° [αD ] + 132° (ε 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-771fda40cb2e4ae2ab743b6066e8bbbe
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03983111

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