Acetic Acid → alpha-(2,4-diflurophenyl)-N-[dimethyl(methoxymethoxymethyl)methyl]nitrone

HRID 636737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636737
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([N+:19]([O-])=[O:20])([CH3:18])[CH2:13][O:14][CH2:15][O:16][CH3:17].C(O)(=O)C>C(O)C.[Zn]>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[N+:19]([C:12]([CH3:18])([CH3:11])[CH2:13][O:14][CH2:15][O:16][CH3:17])[O-:20]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 737702,4-DifluorobenzaldehydeHCID 212556992-Methyl-2-nitro-1-(methoxymethoxy)propane

Produkt 1

HCID 73691529alpha-(2,4-diflurophenyl)-N-[dimethyl(methoxymethoxymethyl)methyl]nitroneAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 2,4-difluorobenzaldehyde (293.3 mg, 2.06 mmol), 2-methyl-2-nitro-1-(methoxymethoxy)propane (382.7 mg, 2.35 mmol) and zinc (266 mg, 4.07 mmol) in ethanol (5 ml) was cooled to 0° C. in ice-water bath. Acetic acid (0.46 ml, 8.0 mmol) was added dropwise to the mixture. The mixture was gradually warmed to room temperature and stirred for 19 hours. The mixture was filtered through Celite® bed and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=4/1) to give the title compound (361.9 mg; 56%).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite® bed
  2. concentrationthe filtrate was concentrated
  3. custompurified by silica gel chromatography (hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-7c8d14fe609c41a4bc7ee26a44e99b1a
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194461B1

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