1,4-Dioxane → HCID 59256611, compound

HRID 640795Notes

Reaction equation

HRID 640795 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([Cl:21])=[CH:11][C:12]([Cl:20])=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[N:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:22]1CCOCC1>O>[CH2:1]([O:8][C:9]1[C:10]([Cl:21])=[CH:11][C:12]([Cl:20])=[C:13]2[C:18]=1[N:17]=[C:16]([CH:19]=[O:22])[CH:15]=[N:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 59256698HCID 59256698, compound

Product 1

HCID 59256611HCID 59256611, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of the 2-methyl product from Step B (93 mg, 0.291 mmol) and SeO2 (100 mg) in dioxane (4 mL) and H2O (0.4 mL) was heated under reflux for 3 h. The mixture was cooled, filtered (celite), and concentrated. Dichloromethane was added and the insoluble material was filtered off. The solvent was evaporated and the residue purified by SiO2-gel chromatography (dichloromethane) to yield the desired aldehyde as an off-white solid (57 mg, 59%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered (celite)
  5. concentrationconcentrated
  6. additionDichloromethane was added
  7. filtrationthe insoluble material was filtered off
  8. customThe solvent was evaporated
  9. customthe residue purified by SiO2-gel chromatography (dichloromethane)

Sources & evidence

ORD record
ord-5999b4494feb43de9b80ccfdec9fc3db
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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