Selenium Dioxide → HCID 86707512, compound

HRID 339011Notes

Reaction equation

HRID 339011 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH2:13][C@@H:14]([OH:16])[CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Se](=O)=[O:18]>O1CCOCC1.O>[OH:16][C@@H:14]([CH3:15])[CH2:13][O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH:1]=[O:18])[CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 81847575(2S)-1-[(2-Methyl-8-quinolinyl)oxy]-2-propanol

Product 1

HCID 86707512HCID 86707512, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-1-(2-methylquinolin-8-yloxy)propan-2-ol (0.15 g, 0.69 mmol) in dioxane (10 mL) and water (0.1 mL) was added selenium dioxide (0.092 g, 0.83 mmol) and the resultant mixture heated at reflux for 2.5 hours. The cooled reaction mixture was filtered through a plug of Celite® to remove solids, rinsing with dichloromethane, and the filtrate was concentrated under reduced pressure. The residue was purified by normal phase chromatography on silica gel (20-40% ethyl acetate/hexanes) providing the title compound (0.091 g, 57%).

Workup

  1. temperatureat reflux for 2.5 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. customThe residue was purified by normal phase chromatography on silica gel (20-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-daad56269f944f7088d08d02ef073242
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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