Benzaldehyde → HCID 18182251, compound

HRID 1359310Notes

Reaction equation

HRID 1359310 reaction equation
C([Li])(C)(C)C.BrC1C(C)=CC(C)=CC=1C.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[N:18]=1.[CH:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O.O1CCCC1.CCCCC>[Cl:16][C:17]1[N:18]=[C:19]([O:23][CH3:24])[C:20]([CH:25]([OH:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 684732-BromomesityleneHCID 870092-Chloro-6-methoxypyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 18182251HCID 18182251, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

100 ml of a pentane solution containing 1.56 mol of tert-butyllithium was slowly added dropwise into a solution of 200 ml of tetrahydrofuran containing 11.9 ml of 2-bromomesitylene at −78° C. under cooling. After stirring at the same temperature for one hour, 7.2 ml of 2-chloro-6-methoxypyridine was slowly added dropwise thereinto. After stirring under ice-cooling for one hour and then at room temperature for one hour, 8.5 ml of benzaldehyde was added thereto under ice-cooling, followed by stirring at room temperature for further one hour. Water was added to the reaction solution, followed by extracting with ethyl acetate. The organic phase was washed with brine and the solvent was removed. The residue was subjected to silica gel column chromatography and eluted with hexane and then with hexane/ethyl acetate (7:1), to give 15.0 g of the target compound.

Workup

  1. temperatureunder cooling
  2. stirringAfter stirring under ice-
  3. temperaturecooling for one hour
  4. waitat room temperature for one hour
  5. temperatureunder ice-cooling
  6. stirringby stirring at room temperature for further one hour
  7. extractionby extracting with ethyl acetate
  8. washThe organic phase was washed with brine
  9. customthe solvent was removed
  10. washeluted with hexane

Sources & evidence

ORD record
ord-b7c580d91af44b21b734b421fad5882b
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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