Diethyl Ether → 2,3,5-Triphenylpyrazine

HRID 1479123ノート

反応式

HRID 1479123 の反応式
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

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 8909Butyl etherHCID 2439072,3-DiphenylpyrazineHCID 178506676HCID 178506676、化合物

生成物 1

HCID 124306492,3,5-Triphenylpyrazine収率 56%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-93d68059f45f468d81f0b48545f78e86
出典データセット
uspto-grants-2016_08
特許番号
US09406895B2

反応ノート

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