Diethyl Ether → 2,3,5-Triphenylpyrazine

HRID 1471322Notes

Reaction equation

HRID 1471322 reaction equation
C(OCCCC)CCC.[C:10]1([Li])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)C.[C:22]1([C:28]2[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:32][CH:31]=[CH:30][N:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[C:22]1([C:28]2[C:33]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[N:32][C:31]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:30][N:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8909Butyl etherHCID 2439072,3-DiphenylpyrazineHCID 178506676HCID 178506676, compound

Product 1

HCID 124306492,3,5-TriphenylpyrazineYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 5.5 mL of a dibutyl ether solution of phenyl lithium (manufactured by Wako Pure Chemical Industries, Ltd., 2.1 mol/L) and 50 mL of diethyl ether were mixed under a nitrogen atmosphere. Then, 2.43 g of 2,3-diphenylpyrazine was dropped into this solution while the solution was being cooled, with ice, and the mixture was stirred at room temperature for 24 hours. Water was added to the mixture, and the organic layer was extracted with diethyl ether. The extracted organic layer was washed with water and dried with magnesium sulfate. After the drying, an excess amount of activated manganese dioxide was added to the organic layer, and the mixture was filtered. After the solvent of the solution was distilled off, the obtained residue was recrystallized with ethanol to give a pyrazine derivative, Htppr (a yellow powder, 56% yield). The synthetic scheme of Step 1 is represented by (a-1) below.

Workup

  1. temperaturewas being cooled, with ice
  2. extractionthe organic layer was extracted with diethyl ether
  3. washThe extracted organic layer was washed with water
  4. dry with materialdried with magnesium sulfate
  5. additionAfter the drying, an excess amount of activated manganese dioxide was added to the organic layer
  6. filtrationthe mixture was filtered
  7. distillationAfter the solvent of the solution was distilled off
  8. customthe obtained residue was recrystallized with ethanol

Sources & evidence

ORD record
ord-59c51348ec1e4892ad44b441a66370c5
Source dataset
uspto-grants-2015_04
Patent number
US09012036B2

Reaction notes

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