Sodium hydride → (4-Bromo-7-methoxy-6-nitro-2,3-dihydro-1H-inden-1-ylidene)acetonitrile

HRID 340682노트

반응식

HRID 340682 반응식
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[Br:14][C:15]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[C:21]([O:27][CH3:28])=[C:20]2[C:16]=1[CH2:17][CH2:18][C:19]2=O.[Cl-].[NH4+]>O1CCCC1>[Br:14][C:15]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[C:21]([O:27][CH3:28])=[C:20]2[C:16]=1[CH2:17][CH2:18][C:19]2=[CH:5][C:3]#[N:4]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 577812634-Bromo-7-methoxy-6-nitro-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 67355123(4-Bromo-7-methoxy-6-nitro-2,3-dihydro-1H-inden-1-ylidene)acetonitrile수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of 60% sodium hydride (1.03 g, 25.6 mmol) in tetrahydrofuran (100 mL) was added diethyl cyanomethylphosphonate (4.52 mL, 28.0 mmol) under ice-cooling, and the mixture was stirred for 15 min. Thereto was added a solution of 4-bromo-7-methoxy-6-nitroindan-1-one (6.67 g, 23.3 mmol) in tetrahydrofuran (50 mL), and the mixture was further stirred for 30 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (5.54 g, yield 77%).

후처리

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

출처 및 근거

ORD 기록
ord-7ad5d280a0494d4e9f7854a6a97abc36
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895591B2

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