3,4-Dimethoxyphenyl methyl ketone → (E)-1-(3,4-dimethoxyphenyl)-3-(dimethylamino)-2-propen-1-one

HRID 1914790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914790
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)=[O:3].[CH3:14][N:15]([CH:17](OC)OC)[CH3:16]>CN(C=O)C>[CH3:14][N:15]([CH:17]=[CH:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)=[O:3])[CH3:16]

Komponenten

4

Edukt 2

HCID 143283,4-Dimethoxyphenyl methyl ketoneHCID 78373Dimethylformamide dimethyl acetal

Produkt 1

HCID 1481361(E)-1-(3,4-dimethoxyphenyl)-3-(dimethylamino)-2-propen-1-oneAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 3,4-dimethoxy acetophenone 11 (5 g, 27.47 mmol) and DMF-DMA (3.9 g, 111.1 mmol) in DMF (10 mL) was heated to 150° C. under an atmosphere of N2. After stirring for 35 h 150° C., the reaction mixture was concentrated in vacuo. The resulting residue was triturated with diethylether and dried under high vacuum to afford compound 12 (5.0 g, 77%) as a yellow solid. TLC Rf=0.5 (CHCl3-MeOH, 9:1); 1H NMR (CDCl3) δ 7.8 (d, J=12.2 Hz, 1H), 7.56-7.51 (m, 3H), 6.86 (d, J=8.1 Hz, 1H), 5.71 (d, J=12.2 Hz, 1H), 3.95 (s, 3H), 3.92 (s, 3H), 3.03 (br, 6H); MS (ES) m/z 236 (M+H+).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe resulting residue was triturated with diethylether
  3. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1d98154f77dd49eeb526a99b40dfe3df
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614237B2

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