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

HRID 1576793ノート

反応式

HRID 1576793 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-771fda40cb2e4ae2ab743b6066e8bbbe
出典データセット
uspto-grants-1976_09
特許番号
US03983111

反応ノート

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