1,4-Dioxane → 7-(2-(Tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehyde

HRID 339062Notes

Reaction equation

HRID 339062 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH3:22])=[N:19]2)=[CH:14][C:13]=1[F:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:24]1CCOCC1>O>[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH:22]=[O:24])=[N:19]2)=[CH:14][C:13]=1[F:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 709833797-(2-(Tert-butyldimethylsilyloxy)ethoxy)-6-fluoro-2-methylquinoline

Product 1

HCID 867075467-(2-(Tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehydeYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 7-(2-(tert-butyldimethylsilyloxy)ethoxy)-6-fluoro-2-methylquinoline (2.74 g, 8.17 mmol) in dioxane (24 mL) and water (0.24 mL) was added SeO2 (0.997 g, 8.98 mmol). The reaction mixture was heated at reflux for 4 hours. After cooling to ambient temperature, the solid was removed by filtration and washed with DCM. The filtrate was concentrated under reduced pressure and The residue was purified by flash chromatography on silica gel (4:1 hexanes/EtOAc) to give 7-(2-(tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehyde (2.69 g, 94%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. customthe solid was removed by filtration
  4. washwashed with DCM
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-ac39514543f8479997cab4ae1c92463c
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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