Selenious Acid → (6-Chloro-3-formyl-quinoxalin-5-yl)-acetic acid methyl ester

HRID 505232

反応式

HRID 505232 の反応式
[Se](O)(O)=[O:2].[CH3:5][O:6][C:7](=[O:21])[CH2:8][C:9]1[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]2[C:10]=1[N:11]=[C:12]([CH3:20])[CH:13]=[N:14]2>O1CCOCC1.O>[CH3:5][O:6][C:7](=[O:21])[CH2:8][C:9]1[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]2[C:10]=1[N:11]=[C:12]([CH:20]=[O:2])[CH:13]=[N:14]2

参加物

5

反応物 2

HCID 1091Selenious Acid2 回HCID 66882129(6-Chloro-3-methyl-quinoxalin-5-yl)-acetic acid methyl ester

生成物 1

HCID 86253938(6-Chloro-3-formyl-quinoxalin-5-yl)-acetic acid methyl ester収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Selenious acid (645 mg, 5.00 mmol, 1.1 equiv) was added to a solution of (6-chloro-3-methyl-quinoxalin-5-yl)-acetic acid methyl ester in dioxane (30 ml). The reaction mixture was heated to 100° C. After 60 minutes, an additional portion of selenious acid (645 mg) was added, and heating was continued for another 60 minutes. After cooling, the reaction mixture was diluted with water, filtered, and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via flash chromatography (gradient of hexane/EtOAc 100:0 to 80:20) to afford the title compound (966 mg, 81%). MS (ES+): 264 (M+H)+.

後処理

  1. temperatureheating
  2. waitwas continued for another 60 minutes
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified via flash chromatography (gradient of hexane/EtOAc 100:0 to 80:20)

出典と根拠

ORDレコード
ord-a31cc0070def436684d8bf55185ce669
出典データセット
uspto-grants-2010_08
特許番号
US07781438B2

関連ノート

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