Acetonitrile → 4-(3,4-Dimethoxyphenyl)-3-oxo-butyronitrile

HRID 506148

Reaktionsgleichung

Reaktionsgleichung von HRID 506148
C([Li])CCC.[C:6](#[N:8])[CH3:7].C[O:10][C:11](=O)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1.[Cl-].[NH4+]>C1COCC1>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([CH2:12][C:11](=[O:10])[CH2:7][C:6]#[N:8])[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 25517Ammonium ChlorideHCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl esterHCID 178418339Butyllithium

Produkt 1

HCID 125197054-(3,4-Dimethoxyphenyl)-3-oxo-butyronitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a 1.0 L three-necked round-bottomed flask was added 50 mL of THF and the reaction mixture was cooled to −78° C. Butyl lithium (BuLi, 1.6 M, 14.4 mL, 23 mmol) was added dropwise keeping the temperature below −70° C. Acetonitrile (1.3 mL, 25 mmol) in 30 mL of THF was added dropwise to the flask amidst stirring and cooling. After 2 hours (h) of stirring, (3,4-dimethoxyphenyl)acetic acid methyl ester (2.3 g, 11 mmol) was added to the resulting white colloidal mixture in the flask. The reaction mixture was stirred for a further 2 h, followed by the addition of saturated ammonium chloride solution (NH4Cl, 75 mL) at −78° C. The organic layer was separated, dried with sodium sulfate (Na2SO4), filtered to remove the drying agent and evaporated to dryness to give the crude product. This crude product was purified by silica gel column chromatography, eluting with 30-70% ethyl acetate (EtOAc) in hexanes to yield 4-(3,4-dimethoxyphenyl)-3-oxo-butyronitrile in the form of a solidifying amber oil, 1.8 g (75%).

Aufarbeitung

  1. customthe temperature below −70° C
  2. temperaturecooling
  3. stirringAfter 2 hours (h) of stirring
  4. stirringThe reaction mixture was stirred for a further 2 h
  5. customThe organic layer was separated
  6. dry with materialdried with sodium sulfate (Na2SO4)
  7. filtrationfiltered
  8. customto remove the drying agent
  9. customevaporated to dryness
  10. customto give the crude product
  11. customThis crude product was purified by silica gel column chromatography
  12. washeluting with 30-70% ethyl acetate (EtOAc) in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-18ffdcc372ca4db49416ce42c4107be2
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781591B2

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