4-Ethoxybenzaldehyde → alpha-(4Ethoxyphenyl)-N-cyclopentylnitrone

HRID 2305802

Reaktionsgleichung

Reaktionsgleichung von HRID 2305802
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:2].[CH:12]1([NH:17][OH:18])[CH2:16][CH2:15][CH2:14][CH2:13]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[N+:17]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[O-:18])=[CH:6][CH:5]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 248344-EthoxybenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 10219393N-cyclopentylhydroxylamine

Produkt 1

HCID 86587908alpha-(4Ethoxyphenyl)-N-cyclopentylnitroneAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Ethoxybenzaldehyde (22.0 g, 0.1467 mol) and N-cyclopentylhydroxylamine (14.1 g, 0.1398 mol) were mixed into toluene (200 mL) with p-toluenesulfonic acid monohydrate (1.0 g, 5.26 mmol). The mixture was refluxed for 3 hrs under argon atmosphere with a Dean-Stark trap to remove generated water. The solution was rotary evaporated to give a residue which was purified by flash chromatography over silica gel with EtOAc as an eluant and then recrystallization from a mixed solvent of hexanes and EtOAc. The title compound was obtained as a solid (21.24 g 65.1% yield), m.p. 95.1° C. (Rf=0.18 on a silica gel plate using hexanes:EtOAc, 2:1, v/v, as an eluant).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 hrs under argon atmosphere with a Dean-Stark trap
  2. customto remove
  3. customThe solution was rotary evaporated
  4. customto give a residue which
  5. customwas purified by flash chromatography over silica gel with EtOAc as an eluant
  6. customrecrystallization from a mixed solvent of hexanes and EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-efc8ac3360094897a3844caea96201e7
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06441032B1

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