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Sodium hydride → ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-fluoro-2-butenoate

HRID 378383
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HRID 378383 반응식
[H-].[Na+].[F:3][CH:4](P(OCC)(OCC)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:18][CH:19]([N:21]1[C:30]2[C:25](=[CH:26][C:27]([C:31](=O)[CH3:32])=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1)[CH3:20].[Cl-].[NH4+]>CN(C)C=O>[CH3:20][CH:19]([N:21]1[C:30]2[C:25](=[CH:26][C:27](/[C:31](/[CH3:32])=[C:4](/[F:3])\[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1)[CH3:18]
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참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 107751501-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl)ethanone

생성물 1

HCID 10852120ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-fluoro-2-butenoate

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

450 mg (60%, 12 mmol) of sodium hydride was suspended in 10 ml of N,N-dimethylformamide. 3.3.g (14 mmol) of ethyl 2-fluoro-diethylphosphonoacetate was dropped into the suspension under cooling with ice. The obtained mixture was stirred under cooling with ice for 30 minutes, followed by the addition of 2.0 g (9.2 mmol) of 1-[1-(1-methylethyl)-1,2,3,4-tetrahydro-quinolin-6-yl)ethanone. The obtained mixture was stirred under cooling with ice for one hour, followed by the addition of an aqueous solution of ammonium chloride. The obtained mixture was extracted with ethyl acetate, and the organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated in a vacuum. The residue was purified by silica gel column chromatography to give 2.3 g of the title compound as a colorless oil.

후처리

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice for 30 minutes
  3. stirringThe obtained mixture was stirred
  4. temperatureunder cooling with ice for one hour
  5. extractionThe obtained mixture was extracted with ethyl acetate
  6. washthe organic phase was washed with a saturated aqueous solution of common salt
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in a vacuum
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a291df216e6c40d6af090468a0ce3b61
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06030964

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