Potassium Hydroxide → 1-(2,6-Dimethyl-4-(pyrazin-2-ylthio)phenyl)ethanone

HRID 1465540노트

반응식

HRID 1465540 반응식
O[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.[N:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[SH:19].[OH-].[K+]>CN(C=O)C.O.[Cu-]=O>[CH3:8][C:6]1[CH:7]=[C:2]([S:19][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][N:13]=2)[CH:3]=[C:4]([CH3:12])[C:5]=1[C:9](=[O:11])[CH3:10]

참가 물질

7

반응물 3

HCID 14797Potassium HydroxideHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanoneHCID 178527737HCID 178527737, 화합물

생성물 1

HCID 866908421-(2,6-Dimethyl-4-(pyrazin-2-ylthio)phenyl)ethanone수율 25%

시약·촉매·용매 3

HCID 178419072HCID 178419072, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1-(4-iodo-2,6-dimethylphenyl)ethanone (4-2, 3.20 g, 11.7 mmol), pyrazine-2-thiol (11-1, 1.96 g, 17.5 mmol), copper(I) oxide (83.5 mg, 0.6 mmol), and potassium hydroxide (1.64 g, 29.2 mmol) in DMF (9.6 mL) and H2O (2.4 mL) was heated at reflux for 24 h. The mixture was quenched with H2O (10 mL) and extracted with ether (2×50 mL). The organic layer was collected, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (3.0% EtOAc in hexanes as eluant) to provide 1-(2,6-dimethyl-4-(pyrazin-2-ylthio)phenyl)ethanone (11-3, 755.2 mg) as yellow oil in 25% yield: 1H NMR (500 MHz, CDCl3) δ 8.47 (s, 1 H), 8.27 (s, 1 H), 8.22 (s, 1 H), 7.28 (s, 2 H), 2.51 (s, 3 H), 2.28 (s, 6 H); ESI-MS: m/z 259.3 (M+H)+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. customThe mixture was quenched with H2O (10 mL)
  4. extractionextracted with ether (2×50 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over MgSO4(s)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (3.0% EtOAc in hexanes as eluant)

출처 및 근거

ORD 기록
ord-533711d0e59c439e8139fe30a76707b4
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999983B2

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