Selenium Dioxide → (R)-8-(1-(tert-butyldimethylsilyloxy)propan-2-yloxy)quinoline-2-carbaldehyde

HRID 339008Notes

Reaction equation

HRID 339008 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([O:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[C:20]([CH3:23])[CH:19]=[CH:18]2)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Se](=O)=[O:25]>O1CCOCC1.O>[Si:1]([O:8][CH2:9][C@H:10]([O:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[C:20]([CH:23]=[O:25])[CH:19]=[CH:18]2)[CH3:11])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 86707508HCID 86707508, compound

Product 1

HCID 86707509(R)-8-(1-(tert-butyldimethylsilyloxy)propan-2-yloxy)quinoline-2-carbaldehydeYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-8-(1-(tert-butyldimethylsilyloxy)propan-2-yloxy)-2-methylquinoline (0.33 g, 1.0 mmol) in dioxane (40 mL) and water (0.4 mL) was added selenium dioxide (0.13 g, 1.2 mmol) and the resultant mixture heated at reflux for 1 hour. 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 (10% ethyl acetate/hexanes) providing the title compound (0.29 g, 84%).

Workup

  1. temperatureat reflux for 1 hour
  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 (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fd936405b487451cb4094576017d6eea
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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