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

HRID 1095754Notes

Reaction equation

HRID 1095754 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-carbaldehyde

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 then all the filtrates were concentrated in vacuo. The crude mixture was chromatographed on silica gel, eluting with a gradient of 1-5% Et2O/hexanes, (0.515 g). 1H NMR (400 MHz, CDCl3) δ 10.19 (s, 1H), 8.18 (d, J =8.7 Hz, 1H), 8.01 (d, J=8.4 Hz, 1H), 7.14-7.08 (m, 1H), 7.06-7.00 (m, 1H), 1.52-1.41 (m, 3H), 1.16 (d, 18H).

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
  6. concentrationall the filtrates were concentrated in vacuo
  7. customThe crude mixture was chromatographed on silica gel
  8. washeluting with a gradient of 1-5% Et2O/hexanes, (0.515 g)

Sources & evidence

ORD record
ord-c4f05fb411ba426cae26530e6d72ad6a
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

Loading…