Water → 1-[2-(1,3-Dioxolan-2-yl)ethyl]-6-fluoroquinoxalin-2(1H)one

HRID 1847086노트

반응식

HRID 1847086 반응식
[H-].[Li+].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH:8]=[N:7]2.Br[CH2:16][CH2:17][CH:18]1[O:22][CH2:21][CH2:20][O:19]1.O>CN(C)C=O>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[CH2:17][CH2:16][N:10]1[C:11]2[C:6](=[CH:5][C:4]([F:3])=[CH:13][CH:12]=2)[N:7]=[CH:8][C:9]1=[O:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 62714Lithium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 126863866-Fluoro-1,2-dihydroquinoxalin-2-one

생성물 1

HCID 867250091-[2-(1,3-Dioxolan-2-yl)ethyl]-6-fluoroquinoxalin-2(1H)one수율 32%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Lithium hydride (57 mg, 7.3 mmol) was added to a solution of 6-fluoroquinoxalin-2(1H)one (1 g, 6.0 mmol) in N,N-dimethylformamide (6 ml) under cooling on ice and the mixture was stirred at room temperature for 30 minutes. The mixture was cooled on ice again and a solution of 2-(2-bromoethyl)-1,3-dioxolane (0.88 ml, 7.3 mmol) in N,N-dimethylformamide (2 ml) was gradually added thereto and the mixture was stirred for 4 hours. Water was added thereto, the mixture was then extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 0.5 g (32%) of the title compound.

후처리

  1. temperatureunder cooling on ice
  2. temperatureThe mixture was cooled on ice again
  3. stirringthe mixture was stirred for 4 hours
  4. extractionthe mixture was then extracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-6d0acef788034ee3b21b7f58af07c8d3
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952010B2

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