Water → 1-{4-((5-Methoxypyrazin-2-yl)oxy)-2,6-dimethylphenyl}ethanone

HRID 1465550노트

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HRID 1465550 반응식
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.Br[C:14]1[CH:19]=[N:18][C:17]([O:20][CH3:21])=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[Cu]>[CH3:21][O:20][C:17]1[N:18]=[CH:19][C:14]([O:1][C:2]2[CH:3]=[C:4]([CH3:12])[C:5]([C:9](=[O:11])[CH3:10])=[C:6]([CH3:8])[CH:7]=2)=[N:15][CH:16]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanoneHCID 197561722-Bromo-5-methoxypyrazine

생성물 1

HCID 866908551-{4-((5-Methoxypyrazin-2-yl)oxy)-2,6-dimethylphenyl}ethanone수율 50%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A mixture of 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (4-2, 3.50 g, 21.3 mmol), 2-bromo-5-methoxypyrazine (6.04 g, 32.0 mmol), copper (271 mg, 4.26 mmol), and potassium carbonate (8.84 g, 64.0 mmol) in 35.5 mL of DMF was stirred at 100° C. overnight. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4(s), concentrated under reduced pressure, and purified by column chromatography on silica gel (20% EtOAc in hexanes as eluant) to give 1-{4-((5-methoxypyrazin-2-yl)oxy)-2,6-dimethylphenyl}ethanone (15-1, 2.90 g) as yellow oils: 1H NMR (500 MHz, CDCl3) δ 7.92 (s, 1 H), 7.87 (s, 1 H), 6.72 (s, 2 H), 3.96 (s, 3 H), 2.47 (s, 3 H), 2.24 (s, 6 H).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4(s)
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography on silica gel (20% EtOAc in hexanes as eluant)

출처 및 근거

ORD 기록
ord-ded4f6de734642eb863c5092bd79892c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999983B2

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