1,4-Dioxane → 72804-91-2

HRID 338867Notes

Reaction equation

HRID 338867 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[CH:8]2)[CH3:2].[O:14]1CCOCC1>O>[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH:13]=[O:14])[CH:9]=[CH:8]2)[CH3:2]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 144752508-Ethyl-2-methylquinoline

Product 1

HCID 1269983472804-91-2Yield 85.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8-ethyl-2-methylquinoline (3.34 g, 19.5 mmol) in dioxane (150 mL) and water (1.5 mL) was added SeO2 (2.60 g, 23.4 mmol) and the mixture was stirred at reflux for 2 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 (1:1 hexane/DCM) to give 8-ethylquinoline-2-carbaldehyde (3.1 g, 85.8%) as a solid.

Workup

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

Sources & evidence

ORD record
ord-917b3a8ce8664f37b43843fb55db1307
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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