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

HRID 343303

反応式

HRID 343303 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 (2a, 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, then quenched with 2-propanol, and extracted with EtOAc. The combined organic layers were washed with H2O, then with saturated aqueous NaCl, and 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 approximately 0.185 g of 5 (62% yield), m.p. 154°-157° C.

後処理

  1. customquenched with 2-propanol
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O
  4. dry with materialwith saturated aqueous NaCl, and dried (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-a8501990f77f478391e18e93927f23a9
出典データセット
uspto-grants-1999_01
特許番号
US05861388

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