Selenium Dioxide → 6-Fluoro-8-(triisopropylsilyloxy)quinoline-2-carbaldehyde

HRID 2035573Notes

Reaction equation

HRID 2035573 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:11]=1)[N:8]=[C:7]([CH3:23])[CH:6]=[CH:5]2.[Se](=O)=[O:25]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:15])[CH3:16])[CH:11]=1)[N:8]=[C:7]([CH:23]=[O:25])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 667814296-Fluoro-2-methyl-8-(triisopropylsilyloxy)quinoline

Product 1

HCID 866386106-Fluoro-8-(triisopropylsilyloxy)quinoline-2-carbaldehydeYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6-fluoro-2-methyl-8-(triisopropylsilyloxy)quinoline (1.76 g, 5.29 mmol) was dissolved in dioxane (58 mL) and water (0.49 mL). The reaction was treated with selenium dioxide (0.76 g, 6.8 mmol) and the mixture was heated to reflux for 13 hours. The mixture was cooled and filtered through GF/F paper. The filtered solids were washed with Et2O and all the filtrates were concentrated in vacuo. The crude mixture was chromatographed on SiO2 eluting with a gradient of 1-5% Et2O/hexanes to provide the desired product (0.515 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 13 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through GF/F paper
  5. washThe filtered solids were washed with Et2O and all the filtrates
  6. concentrationwere concentrated in vacuo
  7. customThe crude mixture was chromatographed on SiO2 eluting with a gradient of 1-5% Et2O/hexanes

Sources & evidence

ORD record
ord-dce5bba7997e4d369fb3601d48ba9394
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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