Chloromethyl Methyl Ether → HCID 86749474, Verbindung

HRID 439612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 439612
[H-].[Na+].[CH:3](=[C:10]1/[C:11](=[O:29])[NH:12][C:13](=[O:28])/[C:14]/1=[CH:15]/[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)\[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:30][O:31][CH2:32]Cl>CN(C)C=O>[CH3:30][O:31][CH2:32][N:12]1[C:13](=[O:28])/[C:14](=[CH:15]/[C:16]2[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=2)/[C:10](=[CH:3]\[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:11]1=[O:29]

Komponenten

5

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 6438903T 686

Produkt 1

HCID 86749474HCID 86749474, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of 63.2% sodium hydride (0.38 g) in dimethylformamide (10 ml) is added dropwise a solution of (3E,4E)-3-benzylidene-4-(3,4,5-trimethoxybenzylidene)-2,5-pyrrolidinedione (3.65 g) in dimethylformamide (10 ml) under ice-cooling, and the mixture is stirred at room temperature for one hour. To the mixture is added dropwise methoxymethyl chloride (0.84 ml) under ice-cooling, and the mixture is stirred at room temperature overnight. The mixture is evaporated to remove the solvent, and to the residue is added ethyl acetate. The mixture is washed, dried, and evaporated to remove the solvent. The resulting residue is purified by silica gel column chromatography (solvent; n-hexane:trichloromethane:ethyl acetate=5:5:4) to give (3E,4E)-1-methoxymethyl-3-benzylidene-4-(3,4,5-trimethoxybenzylidene)-2,5-pyrrolidinedione (3.0 g) as yellow crystals.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture is stirred at room temperature overnight
  4. customThe mixture is evaporated
  5. customto remove the solvent
  6. additionto the residue is added ethyl acetate
  7. washThe mixture is washed
  8. customdried
  9. customevaporated
  10. customto remove the solvent
  11. customThe resulting residue is purified by silica gel column chromatography (solvent; n-hexane:trichloromethane:ethyl acetate=5:5:4)

Quellen und Nachweise

ORD-Eintrag
ord-0362a84fe29840dc9668cdda63b501fd
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05514815

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