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

HRID 1003181

반응식

HRID 1003181 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7c1f5616113040989fdffd0be9eb7133
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046186

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