1,4-Dioxane → HCID 59497123, compound

HRID 2046521Notes

Reaction equation

HRID 2046521 reaction equation
[CH3:1][C:2]1[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[CH:8][CH:7]=[N:6]3)[N:3]=1.[O:19]1CCOCC1>O>[CH2:17]([O:16][C:14]1[C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[CH:8][CH:7]=[N:6]3)[N:3]=[C:2]([CH:1]=[O:19])[CH:15]=1)[CH3:18]

Participants

4

Reactant 2

HCID 312751,4-Dioxane2×HCID 59497119HCID 59497119, compound

Product 1

HCID 59497123HCID 59497123, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of SeO2 (1.01 g, 9.1 mmol) in a mixture of dioxane (50 mL) and water (2 mL) was heated to reflux in a two-neck 250 mL round-bottomed flask. A solution of 2-methyl-4-ethoxy-[1,10]phenanthroline (0.87 g, 3.6 mmol) in hot dioxane (50 mL) was added through an addition funnel over a period of 30 minutes and the reaction mixture was refluxed for 1 hour. The reaction mixture was filtered while hot and the residue rinsed with more hot dioxane (20 mL) and filtered. The filtrates were combined and concentrated in vacuo and the residue was treated with methylene chloride (100 mL) and a 10% K2CO3 aqueous solution (100 mL). The aqueous layer was extracted with methylene chloride (3×100 mL) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography (SiO2, MeOH/DCM, 1:30 to 1:15) to afford the pure product as a light brown solid (0.15 g, 16%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux in a two-neck 250 mL round-bottomed flask
  3. temperaturethe reaction mixture was refluxed for 1 hour
  4. filtrationThe reaction mixture was filtered while hot and the residue
  5. washrinsed with more hot dioxane (20 mL)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionthe residue was treated with methylene chloride (100 mL)
  9. extractionThe aqueous layer was extracted with methylene chloride (3×100 mL)
  10. washthe combined organic layers were washed with brine
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe crude product was purified by flash chromatography (SiO2, MeOH/DCM, 1:30 to 1:15)

Sources & evidence

ORD record
ord-93dbbeab9349475a823a59cf7ba61e41
Source dataset
uspto-grants-2013_11
Patent number
US08592446B2

Reaction notes

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