1-methoxy-N,N,N',N'-tetramethylmethylenediamine → Methyl 2-[4-(benzyloxy)phenyl]-3-dimethylamino-2-propenoate

HRID 270930

Reaktionsgleichung

Reaktionsgleichung von HRID 270930
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.CO[CH:22](N(C)C)[N:23]([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:19])[C:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)=[CH:22][N:23]([CH3:25])[CH3:24]

Komponenten

4

Edukt 2

HCID 709081-methoxy-N,N,N',N'-tetramethylmethylenediamineHCID 2756645Methyl 2-(4-benzyloxyphenyl)acetate

Produkt 1

HCID 69154646Methyl 2-[4-(benzyloxy)phenyl]-3-dimethylamino-2-propenoateAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

According to a modified literature procedure (Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580) a solution of 1.0 g (3.9 mmol) of (4-benzyloxy-phenyl)-acetic acid methyl ester in 4 mL of toluene was flushed with argon. To this solution was added 0.842 mL g (5.5 mmol) of methoxy bis(dimethylamino)methane, and the resulting mixture was stirred at 65° C. under argon overnight. The reaction mixture was concentrated to give 1.21 g of desired 2-(4-benzyloxy-phenyl)-3-dimethylamino-acrylic acid methyl ester as indicated by 1H NMR (containing traces of starting material). The product was used without any further purification in the next step.

Aufarbeitung

  1. customwas flushed with argon
  2. additionTo this solution was added 0.842 mL
  3. concentrationThe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-884efd4914354b898e66186768ebc3d7
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449488B2

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