Potassium Carbonate → 4-(2-[(5,6-Diphenyl-2-pyrazinyl)oxy]ethoxy)benzaldehyde

HRID 968304

Reaction equation

HRID 968304 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([OH:19])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(O[CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][CH:29]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]1([C:7]2[N:8]=[CH:9][C:10]([O:19][CH2:25][CH2:26][O:27][C:28]3[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][CH:29]=3)=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 222886502-(4-Formylphenoxy)ethyl methanesulfonateHCID 178516746HCID 178516746, compound

Product 1

HCID 222886444-(2-[(5,6-Diphenyl-2-pyrazinyl)oxy]ethoxy)benzaldehydeYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture containing 5,6-diphenyl-2-pyrazinol (2.45 g), 4-[2-(methanesulfonyloxy)ethoxy]benzaldehyde (2.44 g), and potassium carbonate (1.8 g), dimethylformamide (100 mL) was added. The resultant mixture was heated at 100° C. on an oil bath for two hours under stirring, and the reaction mixture was poured into an ice-water mixture. The thus-formed organic matter was separated through extraction by use of ethyl acetate, followed by washing sequentially with water and saturated saline. The washed product was dried over sodium sulfate anhydrate, and the residual solvent was removed through distillation under reduced pressure. The thus-yielded residue was purified by means of a silica gel column and crystallized from n-hexane, to thereby yield 3.34 g of the title compound (yield 85.4%).

Workup

  1. additionwas added
  2. customThe thus-formed organic matter was separated through extraction by use of ethyl acetate
  3. washby washing sequentially with water and saturated saline
  4. dry with materialThe washed product was dried over sodium sulfate anhydrate
  5. customthe residual solvent was removed through distillation under reduced pressure
  6. customThe thus-yielded residue was purified by means of a silica gel column
  7. customcrystallized from n-hexane

Sources & evidence

ORD record
ord-9192b5db5b1a4b2bbfd39273c74789b6
Source dataset
uspto-grants-2005_10
Patent number
US06958353B2

Linked notes

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