Water → HCID 22288642, compound

HRID 968305

Reaction equation

HRID 968305 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([O:19][CH2:20][CH2:21][O:22][C:23]3[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=3)=[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.[BH4-].[Na+].O>C(O)C>[C:1]1([C:7]2[N:8]=[CH:9][C:10]([O:19][CH2:20][CH2:21][O:22][C:23]3[CH:24]=[CH:25][C:26]([CH2:27][OH:28])=[CH:29][CH:30]=3)=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 222886444-(2-[(5,6-Diphenyl-2-pyrazinyl)oxy]ethoxy)benzaldehyde

Product 1

HCID 22288642HCID 22288642, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-(2-[(5,6-Diphenyl-2-pyrazinyl)oxy]ethoxy)benzaldehyde (2.90 g) was dissolved in ethanol (30 mL), and sodium borohydride (615 mg) was added to the resultant solution under ice cooling. The mixture was stirred at room temperature for one hour. Subsequently, water was added to the reaction mixture, and the thus-formed organic matter was separated through extraction by use of methylene chloride, followed by washing sequentially by 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 crystallized from n-hexane, to thereby yield 2.69 g of the title compound as colorless crystals (yield 92.3%).

Workup

  1. customthe thus-formed organic matter was separated through extraction by use of methylene chloride
  2. washby washing sequentially by water and saturated saline
  3. dry with materialThe washed product was dried over sodium sulfate anhydrate
  4. customthe residual solvent was removed through distillation under reduced pressure
  5. customThe thus-yielded residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-bec52e880e2d4d408ec9438f2d5dab95
Source dataset
uspto-grants-2005_10
Patent number
US06958353B2

Linked notes

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