Diethyl Ether → 2-Methyl-3-phenylpyrazine

HRID 716478

Reaction equation

HRID 716478 reaction equation
C(OCCCC)CCC.[C:10]1([Li])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)C.[CH3:22][C:23]1[CH:28]=[N:27][CH:26]=[CH:25][N:24]=1>O>[CH3:22][C:23]1[C:28]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:27][CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 79762-MethylpyrazineHCID 8909Butyl etherHCID 178506676HCID 178506676, compound

Product 1

HCID 125688282-Methyl-3-phenylpyrazineYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, in a nitrogen atmosphere, 50 mL of a dibutyl ether solution containing phenyl lithium (produced by Wako Pure Chemical Industries, Ltd, 2.1 mol/L) and 250 mL of diethylether were mixed. Then, 8.98 g of 2-methylpyrazine (produced by Tokyo Chemical Industries Co., Ltd) was dropped into this solution while the solution was being cooled with ice, and stirred at a room temperature for three hours. Water was added into the reacted solution and an organic layer was extracted with diethylether. The obtained organic layer was washed with water and dried with magnesium sulfate. After the solvent was distilled off, the obtained residue was purified by column chromatography using dichloromethane as a developing solvent, thereby obtaining a pyrazine derivative Hmppr (yellow oily matter, yield: 22%). A synthesis scheme of Step 1 is shown by the following (a-1).

Workup

  1. additionwere mixed
  2. temperaturewas being cooled with ice
  3. extractionan organic layer was extracted with diethylether
  4. washThe obtained organic layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-2bd2ed02403a4baab64126dacee7c0f8
Source dataset
uspto-grants-2015_11
Patent number
US09187689B2

Linked notes

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