Diethyl Ether → 2,3,5-Triphenylpyrazine

HRID 1479123노트

반응식

HRID 1479123 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 124306492,3,5-Triphenylpyrazine수율 56%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-93d68059f45f468d81f0b48545f78e86
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09406895B2

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