Acetonitrile → 3-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile

HRID 1917887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1917887
[H-].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]1([C:8](OC)=[O:9])[CH2:7][CH2:6]1.[C:14](#[N:16])[CH3:15]>C1COCC1>[O:9]=[C:8]([C:5]1([C:4]([F:13])([F:12])[F:3])[CH2:7][CH2:6]1)[CH2:15][C:14]#[N:16]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 242087841-(Trifluoromethyl)cyclopropane-1-carboxylic acid methyl ester

Produkt 1

HCID 668764113-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrileAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a slurry of NaH (432 mg, 18 mmol) in THF (40 mL) heated at reflux was added dropwise over 10 minutes a solution of methyl 1-(trifluoromethyl)cyclopropanecarboxylate (2.0 g, 11.9 mmol) in acetonitrile (940 uL, 12 mmol) and the mixture heated at reflux overnight. After cooling to room temperature, the reaction was partitioned between ether and H2O, the aqueous layer acidified with 1N HCl(aq), extracted with ether, and the combined org layers washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography (5-40% EtOAc/hexanes) to give 3-oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile (1.04 g, 5.88 mmol, 49%). LC-MS (ESI) m/z 178 (M+H)+.

Aufarbeitung

  1. temperatureat reflux
  2. temperaturethe mixture heated
  3. temperatureat reflux overnight
  4. customthe reaction was partitioned between ether and H2O
  5. extractionextracted with ether
  6. washthe combined org layers washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by column chromatography (5-40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-19d3b1c10fa0486bbc92a4e0051e67e9
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618289B2

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