Diethyl Ether → 3,5-Dimethyl-2-phenylpyrazine

HRID 716479

反応式

HRID 716479 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.[CH3:22][C:23]1[CH:28]=[N:27][CH:26]=[C:25]([CH3:29])[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]=[C:25]([CH3:29])[N:24]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 79382,6-DimethylpyrazineHCID 8909Butyl etherHCID 178506676HCID 178506676、化合物

生成物 1

HCID 584102943,5-Dimethyl-2-phenylpyrazine収率 16%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

First, in a nitrogen atmosphere, 50 mL of a dibutylether solution containing phenyl lithium (produced by Wako Pure Chemical Industries, Ltd, 2.1 mol/L) and 250 mL of diethyl ether were mixed. Then, 10.33 g of 2,6-dimethylpyrazine was added into this solution while the solution was being cooled with ice, and stirred at a room temperature for 24 hours. Water was added into this mixture and an organic layer was extracted with diethylether. The obtained organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtrated. After the solvent of the filtrate was distilled off, the obtained residue was purified by silicagel column chromatography using dichloromethane as a developing solvent, thereby obtaining an objective pyrazine derivative Hmppr-Me (reddish brown liquid, yield: 16%). A synthesis scheme of Step 1 is shown by the following (a-2).

後処理

  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. filtrationAfter the drying, the solution was filtrated
  7. distillationAfter the solvent of the filtrate was distilled off
  8. customthe obtained residue was purified by silicagel column chromatography

出典と根拠

ORDレコード
ord-d610805445034c689cbb0f645f88b0f1
出典データセット
uspto-grants-2015_11
特許番号
US09187689B2

関連ノート

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