Diglyme → Tjn-331

HRID 428133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 428133
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[C:9]([O:11]C)=O)[CH:2]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:18][CH2:19][NH:20][CH3:21].[H-].[Na+].COCCOCCOC>O>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:18][CH2:19][N:20]([CH3:21])[C:9](=[O:11])/[CH:8]=[CH:7]/[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 8150DiglymeHCID 24758Sodium hydrideHCID 77039N-MethylhomoveratrylamineHCID 53576873-Pyridineacrylic acid, methyl ester

Produkt 1

HCID 9818748Tjn-331Ausbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of methyl trans-3-(3-pyridyl)acrylate (326 mg), 3,4-dimethoxy-N-methylphenethylamine (390 mg), 60% sodium hydride (80 mg) and diethylene glycol dimethyl ether (2 ml) was stirred at room temperature for 24 hours. Water was added to the reaction mixture, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. After the solvent was distilled out under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol=50:1) and recrystallized to yield the titled compound (278 mg, 43%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationAfter the solvent was distilled out under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)
  6. customrecrystallized

Quellen und Nachweise

ORD-Eintrag
ord-e294c8625fed4dccadecbf005de2f81d
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313153B1

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