Triethylamine → (E)-N-methoxy-4-(4-methoxyphenyl)-N-methylbut-3-enamide

HRID 2069623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069623
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[CH2:11][C:12]([OH:14])=O)=[CH:5][CH:4]=1.F[B-](F)(F)F.[N:20]1([O:29][C:30](N(C)C)=[N+](C)C)[C:24]2C=CC=CC=2N=N1.CCN(CC)CC>CN(C=O)C.O>[CH3:30][O:29][N:20]([CH3:24])[C:12](=[O:14])[CH2:11]/[CH:10]=[CH:9]/[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 14713049(E)-4-(4-methoxyphenyl)but-3-enoic acid

Produkt 1

HCID 22347543(E)-N-methoxy-4-(4-methoxyphenyl)-N-methylbut-3-enamideAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To the mixture of carboxylic acid (557) (5.7 g, 29.5 mmol) in DMF (150 mL) was added O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (9.5 g, 29.5 mol). After stifling for 5 minutes, N,O-dimethylhydroxylamine. HCl (2.9 g, 29.5 mmol) was added, followed by Et3N (8.2 mL, 58.9 mmol). The reaction mixture was stirred at room temperature for 3 hours, diluted with water and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (40% EtOAc in hexanes) to provide (E)-N-methoxy-4-(4-methoxyphenyl)-N-methylbut-3-enamide (558) (2.1 g, 29.6%) as a yellow solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (40% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5e9682b6c8f24b9599380cab0c35ef45
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299117B2

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