4-Methyloxybenzyl chloride → HCID 86658014, Verbindung

HRID 70713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70713
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[CH:11]1([C:14]2[C:19](=[O:20])[NH:18][C:17]([CH:21]=[O:22])=[CH:16][CH:15]=2)[CH2:13][CH2:12]1.[Al]>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[CH:11]1([C:14]2[CH:15]=[CH:16][C:17]([CH:21]=[O:22])=[N:18][C:19]=2[O:20][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:13][CH2:12]1

Komponenten

6

Edukt 3

HCID 699934-Methyloxybenzyl chlorideHCID 5359268AluminumHCID 866580135-Cyclopropyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde

Produkt 1

HCID 86658014HCID 86658014, VerbindungAusbeute 105,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

p-Methoxybenzyl chloride (329 mg) was added to a solution of 5-cyclopropyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde (228 mg) in chloroform (10 mL), after which the reaction tube was covered with aluminum foil to provide shading conditions. Silver carbonate (771 mg) was added and the mixture was stirred at room temperature for three hours. The insoluble matter was filtered off and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=92:8→34:66) to give 5-cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridine-2-carbaldehyde as a colorless oil (417 mg, 86%).

Aufarbeitung

  1. customto provide shading conditions
  2. filtrationThe insoluble matter was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=92:8→34:66)

Quellen und Nachweise

ORD-Eintrag
ord-c572a8a4b46340c5917b7d7882651cf1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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