Selenium Dioxide → HCID 86707527, compound

HRID 339030Notes

Reaction equation

HRID 339030 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2)(=[O:3])[CH3:2].[Se](=O)=[O:20]>O1CCOCC1.O>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH:18]=[O:20])[CH:14]=[CH:13]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 70983851HCID 70983851, compound

Product 1

HCID 86707527HCID 86707527, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(2-methylquinolin-8-yloxy)ethyl acetate (0.29 g, 1.2 mmol) in dioxane (20 mL) and water (0.20 mL) was added selenium dioxide (0.16 g, 1.4 mmol) and the resultant mixture heated at reflux for 2 hours. The cooled reaction mixture was filtered through a plug of Celite® to remove solids, rinsing with dichloromethane. The filtrate was concentrated under reduced pressure and purified by normal phase chromatography on silica gel (10-20% ethyl acetate/hexanes) to afford the title compound (0.30 g, 99%).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered through a plug of Celite®
  4. customto remove solids
  5. washrinsing with dichloromethane
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by normal phase chromatography on silica gel (10-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-262f421132b248dfa0217f18cbe30c74
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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