2-Formyl-17beta-estradiol → 3-Hydroxyestra-1,3,5(10)-trien-17-one-2-carboxaldehyde

HRID 1003181

反応式

HRID 1003181 の反応式
[OH:1][C:2]1[C:19]([CH:20]=[O:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C@@H:11]([OH:22])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[OH:1][C:2]1[C:19]([CH:20]=[O:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:22])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 99949802-Formyl-17beta-estradiolHCID 131709961Jones' reagent

生成物 1

HCID 114037863-Hydroxyestra-1,3,5(10)-trien-17-one-2-carboxaldehyde収率 62%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 3,17β-dihydroxyestra-1,3,5(10)-triene-2-carboxaldehyde (57, 0.300 g, 1.0 mmol) in acetone (20 mL) was added Jones reagent (0.5 mL) at 0° C. The reaction mixture was stirred for 5 min, and quenched with 2-propanol, and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (MgSO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:THF (4:1→3:1, v/v) to afford 0.185 g of 60 (62% yield) mp: 154-157° C.

後処理

  1. customquenched with 2-propanol
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. filtrationThe desiccant was filtered
  6. customthe solvent was evaporated at reduced pressure
  7. customThe residue was purified by column chromatography (silica gel)

出典と根拠

ORDレコード
ord-7c1f5616113040989fdffd0be9eb7133
出典データセット
uspto-grants-2000_04
特許番号
US06046186

関連ノート

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