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

HRID 1465540ノート

反応式

HRID 1465540 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178419072HCID 178419072、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-533711d0e59c439e8139fe30a76707b4
出典データセット
uspto-grants-2015_04
特許番号
US08999983B2

反応ノート

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