Selenium Dioxide → HCID 86707475, compound

HRID 338956Notes

Reaction equation

HRID 338956 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:17])[CH:13]=[CH:12]2)[CH3:5].[Se](=O)=[O:19]>O1CCOCC1.O>[CH3:1][O:2][CH2:3][C@H:4]([O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH:17]=[O:19])[CH:13]=[CH:12]2)[CH3:5]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 70982963(R)-8-(1-methoxypropan-2-yloxy)-2-methylquinoline

Product 1

HCID 86707475HCID 86707475, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-8-(1-methoxypropan-2-yloxy)-2-methylquinoline (0.45 g, 1.9 mmol) in dioxane (35 mL) and water (0.35 mL) was added selenium dioxide (0.26 g, 2.3 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 (0.42 g, 88%).

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-b6efd659ac0741f48cedd8092ed6c543
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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