Sodium Carbonate → 2-(4-Methoxy-2-nitrophenyl)acetonitrile

HRID 1913427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913427
C(OC(=O)[CH:5]([C:17]#[N:18])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[N+:14]([O-:16])=[O:15])C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:17]#[N:18])=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=1

Komponenten

4

Edukt 2

HCID 10340Sodium CarbonateHCID 11086625Cyano-(4-methoxy-2-nitro-phenyl)-acetic acid ethyl ester

Produkt 1

HCID 111831262-(4-Methoxy-2-nitrophenyl)acetonitrileAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To cyano-(4-methoxy-2-nitro-phenyl)-acetic acid ethyl ester (945 mg, 3.58 mmol) was added 30 mL of a saturated solution of aqueous sodium carbonate. The mixture was stirred overnight at 55° C. After cooling to room temperature, the mixture was diluted with ethyl acetate. The organic layer was washed with saturated brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified on a Biotage (Biotage Inc.) 10 g silica column, eluting with 0-40% EtOAc in heptanes to provide 258 mg (37%) of (4-methoxy-2-nitro-phenyl)-acetonitrile.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified on a Biotage (Biotage Inc.) 10 g silica column
  6. washeluting with 0-40% EtOAc in heptanes

Quellen und Nachweise

ORD-Eintrag
ord-476090a1aeef4579b2202e504531375b
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609680B2

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