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

HRID 1003181

Reaction equation

HRID 1003181 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7c1f5616113040989fdffd0be9eb7133
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Linked notes

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