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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 378383
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a291df216e6c40d6af090468a0ce3b61
Quelldatensatz
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06030964

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