Diethyl Ether → 2-Phenyl-3-methoxypyrazine

HRID 45567Notes

Reaction equation

HRID 45567 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1.C(OCC)C.C(OCCCC)CCC.[C:23]1([Li])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[C:23]1([C:8]2[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][N:7]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8909Butyl etherHCID 184672-MethoxypyrazineHCID 178506676HCID 178506676, compound

Product 1

HCID 149204992-Phenyl-3-methoxypyrazineYield 12%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, in a three-neck flask, 11.30 g of 2-methoxypyrazine and 200 mL of diethylether were put, and a dibutyl ether solution (2.1 mol/L) of phenyl lithium was dropped thereto while the mixture was cooled down with ices and stirred under a nitrogen atmosphere, and stirred to be reacted for 20 hours. After the reaction, water was added to the reaction solution, and an organic layer was extracted with ethyl acetate. The obtained organic layer was washed with water, and dried with magnesium sulfate. Magnesium sulfate was removed by filtration and the solvent was distilled off. The obtained residue was refined with a column chromatography using dichloromethane as a development solvent, so that 2-phenyl-3-methoxypyrazine was obtained (light yellow powder, yield: 12%). A synthesis scheme of Step 1 is shown by the following (a2-1).

Workup

  1. temperaturewhile the mixture was cooled down with ices
  2. stirringstirred
  3. customto be reacted for 20 hours
  4. additionwas added to the reaction solution
  5. extractionan organic layer was extracted with ethyl acetate
  6. washThe obtained organic layer was washed with water
  7. dry with materialdried with magnesium sulfate
  8. customMagnesium sulfate was removed by filtration
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-66c0084a01944f83a4f46360efaa19c3
Source dataset
uspto-grants-2013_09
Patent number
US08541574B2

Reaction notes

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