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

HRID 505232

반응식

HRID 505232 반응식
[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

참가 물질

5

반응물 2

HCID 1091Selenious Acid2회HCID 66882129(6-Chloro-3-methyl-quinoxalin-5-yl)-acetic acid methyl ester

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a31cc0070def436684d8bf55185ce669
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781438B2

연결된 노트

불러오는 중…