Methyl iodide → (E)-methyl 4-(dimethoxymethyl)cinnamate

HRID 891236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891236
CO[C:3]([O:15][CH3:16])([OH:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][CH:7]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].[CH3:23]I>CN(C)C=O>[CH3:17][O:20][CH:12]([O:13][CH3:23])[C:9]1[CH:8]=[CH:7][C:6](/[CH:5]=[CH:4]/[C:3]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 865896714-Formylcinnamic acid dimethyl acetal

Produkt 1

HCID 23247180(E)-methyl 4-(dimethoxymethyl)cinnamateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

4-Formylcinnamic acid dimethyl acetal (Cleeland, Jr., et al., U.S. Pat. No. 3,969,373) (20.00 g) and anhydrous potassium carbonate (12.44 g) were stirred in anhydrous N,N-dimethylformamide (189 ml) for 5 minutes. Methyl iodide (12.8 g) was added and the resulting mixture was stirred vigorously with gentle heating (oil bath at 40° C.) for 18 h. Volatiles were evaporated in vacuo and the residue partitioned between hexanes (400 ml) and water (100 ml). The hexanes layer was dried (magnesium sulfate) and evaporated to give (E)-methyl 4-(dimethoxymethyl)cinnamate as a pale yellow oil (18.98 g, 89%), 1H-NMR (DMSO-d6) consistent with structure.

Aufarbeitung

  1. customVolatiles were evaporated in vacuo
  2. customthe residue partitioned between hexanes (400 ml) and water (100 ml)
  3. dry with materialThe hexanes layer was dried (magnesium sulfate)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ebaa1c820d2649afa9929bc3f4a06ab6
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07002012B2

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