1,4-Dioxane → HCID 59497139, compound

HRID 2046525Notes

Reaction equation

HRID 2046525 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:19]2[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[CH:14][CH:13]=[N:12]3)[N:9]=[C:8]([CH3:20])[CH:7]=1.[O:21]1CCOCC1>O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:19]2[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[CH:14][CH:13]=[N:12]3)[N:9]=[C:8]([CH:20]=[O:21])[CH:7]=1

Participants

4

Reactant 2

HCID 312751,4-Dioxane2×HCID 59497150HCID 59497150, compound

Product 1

HCID 59497139HCID 59497139, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of SeO2 (1.19 g, 10.8 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 4-(2-methoxy-ethoxy)-2-methyl-[1,10]phenanthroline (1.16 g, 4.3 mmol) in hot dioxane (30 mL) was added through an addition funnel over a period of 10 minutes and the reaction mixture was refluxed for 30 minutes. The solvent was evaporated in vacuo and the residue was treated with methylene chloride (200 mL) and saturated NaHCO3 (200 mL). The aqueous layer was extracted several times with methylene chloride (3×100 mL) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography (SiO2, MeOH/DCM, 1:40 to 1:20) to afford the pure product as a pale solid (0.65 g, 53%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux in a two-neck 250 mL round-bottomed flask
  3. temperaturethe reaction mixture was refluxed for 30 minutes
  4. customThe solvent was evaporated in vacuo
  5. additionthe residue was treated with methylene chloride (200 mL) and saturated NaHCO3 (200 mL)
  6. extractionThe aqueous layer was extracted several times with methylene chloride (3×100 mL)
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was purified by flash chromatography (SiO2, MeOH/DCM, 1:40 to 1:20)

Sources & evidence

ORD record
ord-85f6778721874490962dc4449ab6e0d1
Source dataset
uspto-grants-2013_11
Patent number
US08592446B2

Reaction notes

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