Ethyl Acetate → HCID 58820194, 화합물

HRID 457700

반응식

HRID 457700 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[H-].[Na+].[CH3:12][O:13][C:14](=[O:25])[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][N:18]=[C:17](Cl)[CH:16]=1.CCOC(C)=O>C1COCC1.O>[CH3:12][O:13][C:14](=[O:25])[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][N:18]=[C:17]([O:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:16]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1230512,4-DifluorophenolHCID 45480451Methyl 2-chloro-5-nitroisonicotinate

생성물 1

HCID 58820194HCID 58820194, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To 2,4 difluorophenol (Aldrich Chemical Co.) (2.68 mL, 1.1 eq) in THF (60 mL) at 0° C. was added sodium hydride (60% in oil) (1.123 g, 1.1 eq), and the resulting mixture was stirred from 0° C. to room temperature over 1 hour. This solution was then added to compound (1A) (5.79 g, 26.7 mmol), and the resulting mixture was heated at reflux for 2 hours. TLC analysis confirmed that the reaction was complete, and the mixture was cooled to room temperature. EtOAc (300 mL) and water (100 mL) were added, the resulting mixture was partitioned, and the layers were separated. The organic layer was washed with water (3×100 mL) and brine (1×100 mL). Then the EtOAc layer was dried over magnesium sulfate, filtered, concentrated, and pumped to give the titled compound (1B) as an off-white powder (7.99 g, M+=310, Mp=90.2–91.4° C.)

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthe resulting mixture was partitioned
  4. customthe layers were separated
  5. washThe organic layer was washed with water (3×100 mL) and brine (1×100 mL)
  6. dry with materialThen the EtOAc layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3fddf5fc3147439e9e59f4b03d968e9c
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189731B2

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