Water → 1-(2,6-Dimethyl-4-(pyrazin-2-yloxy)phenyl)ethanone

HRID 1465530노트

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HRID 1465530 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.Cl[C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[Cu]>[CH3:12][C:4]1[CH:3]=[C:2]([O:1][C:14]2[CH:19]=[N:18][CH:17]=[CH:16][N:15]=2)[CH:7]=[C:6]([CH3:8])[C:5]=1[C:9](=[O:11])[CH3:10]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 73277ChloropyrazineHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanone

생성물 1

HCID 866908331-(2,6-Dimethyl-4-(pyrazin-2-yloxy)phenyl)ethanone수율 88%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (4-2, 4.66 g, 28.4 mmol), 2-chloropyrazine (2.50 g, 21.8 mmol), copper (27.7 mg, 4.36 mmol), and potassium carbonate (9.05 g, 65.5 mmol) in 43.7 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 (50% EtOAc in hexanes as eluant) to give 1-(2,6-dimethyl-4-(pyrazin-2-yloxy)phenyl)ethanone (7-1, 4.65 g) as brown oils: 1H NMR (500 MHz, CDCl3) δ 8.43 (bs, 1 H), 8.29 (bs, 1 H), 8.14 (bs, 1 H), 6.83 (s, 2 H), 2.49 (s, 3 H), 2.27 (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 (50% EtOAc in hexanes as eluant)

출처 및 근거

ORD 기록
ord-c979417c5159455b829bfa571419b207
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999983B2

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