Ethyl cyanoacetate → Ethyl 2-cyano-3-[3-(methyloxy)phenyl]-2-butenoate

HRID 2212287

Reaktionsgleichung

Reaktionsgleichung von HRID 2212287
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=O)[CH3:10])[CH:6]=[CH:7][CH:8]=1.[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.C(O)(=O)C.C1C=CC=CC=1>[CH2:18]([O:17][C:15](=[O:16])[C:14]([C:12]#[N:13])=[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:10])[CH3:19]

Komponenten

7

Edukt 3

HCID 7764Ethyl cyanoacetate2×HCID 114603-MethoxyacetophenoneHCID 517165Ammonium Acetate

Produkt 1

HCID 4115002Ethyl 2-cyano-3-[3-(methyloxy)phenyl]-2-butenoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittel2×HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3′-methoxyacetophenone (50 mmole), ethyl cyanoacetate (50 mmole), acetic acid (1.14 mL) ammonium acetate (400 mg), and benzene (50 mL) is heated to reflux in a Dean-Stark apparatus. After approximately 10 hours, additional ethyl cyanoacetate (50 mmole), acetic acid (1.14 mL), and ammonium acetate (400 mg) are added. After an additional 10 hours, the reaction is cooled to room temperature, diluted with ethyl acetate (30 mL), washed with water (240 mL), brine (40 mL), and dried (Na2SO4). After filtering, the extract is concentrated in vacuo and the desired product, as a mixture of E- and Z-isomers, is isolated by column chromatography on silica gel, eluting with 5% ethyl acetate/petroleum ether.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux in a Dean-Stark apparatus
  3. waitAfter an additional 10 hours
  4. washwashed with water (240 mL), brine (40 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationAfter filtering
  7. concentrationthe extract is concentrated in vacuo
  8. additionthe desired product, as a mixture of E- and Z-isomers
  9. customis isolated by column chromatography on silica gel
  10. washeluting with 5% ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-5f9e5946f1734296a7c1a59c9af2489c
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101905B2

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