Methyl iodide → HCID 57544371, Verbindung

HRID 537966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537966
[O-][CH2:2]C.[Na+].[F:5][C:6]([F:23])([F:22])[C:7]1[CH:8]=[C:9]([CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)[C:10]([CH2:12][C:13]#[N:14])=[O:11].CI>CCO>[F:5][C:6]([F:22])([F:23])[C:7]1[CH:8]=[C:9]([C:10](=[O:11])[CH:12]([CH3:2])[C:13]#[N:14])[CH:15]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:17]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 247268153,5-Bis(Trifluoromethyl)Benzoylacetonitrile

Produkt 1

HCID 57544371HCID 57544371, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of sodium ethoxide (0.127 g, 1.87 mmol) in EtOH (5 mL) was treated with 3,5-bis(trifluoromethyl)benzoyl acetonitrile (0.500 g, 1.78 mmol) portionwise over 5 min. The reaction was heated at reflux for 30 min before the addition of methyl iodide (0.41 mL, 6.6 mmol). Heating at reflux was continued for a further 2 h before the reaction mixture was allowed to cool and concentrated in vacuo. The residue was partitioned between H2O (10 mL) and EtOAC (20 mL) and the aqueous phase was separated and re-extracted with EtOAC (2×20 mL). The combined organic extracts were washed with brine (25 mL), dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography on silica gel (0-20% EtOAc in hexanes gradient) to afford 3-[3,5-bis(trifluoromethyl)phenyl]-2-methyl-3-oxopropanenitrile. 1H NMR (500 MHz, CDCl3) δ 8.21 (s, 2H), 8.10 (s, 1H), 4.42 (q, J=7.1 Hz, 1H), 1.71 (d, J=7.1 Hz, 6H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureHeating
  3. temperatureat reflux
  4. temperatureto cool
  5. concentrationconcentrated in vacuo
  6. customThe residue was partitioned between H2O (10 mL) and EtOAC (20 mL)
  7. customthe aqueous phase was separated
  8. extractionre-extracted with EtOAC (2×20 mL)
  9. washThe combined organic extracts were washed with brine (25 mL)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude product was purified by flash chromatography on silica gel (0-20% EtOAc in hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-7f589b786d3b4f268f241abe399fcfee
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865707B2

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