2-((4-Nitrobenzyl)oxy)tetrahydro-2H-pyran → 4-(2-Tetrahydropyranyloxymethyl)aniline

HRID 843101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 843101
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1>C(O)C.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1

Komponenten

4

Edukt 1

HCID 109006552-((4-Nitrobenzyl)oxy)tetrahydro-2H-pyran

Produkt 1

HCID 184721974-(2-Tetrahydropyranyloxymethyl)anilineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-tetrahydropyranyloxymethyl)nitrobenzene (59.7 g, 0.256 mol) in ethanol (EtOH) (300 ml) was added under nitrogen atmosphere at room temperature 10% Pd/C (5.97 g), and catalytic hydrogenation was carried out. The mixture was stirred at room temperature for 24 hours. After the reaction completed, the catalyst was filtered off, and the organic layer was concentrated under reduced pressure. The residue was purified with silica gel column chromatography to give 4-(2-tetrahydropyranyloxymethyl)-aniline (39.7 g, 76%) as syrup.

Aufarbeitung

  1. filtrationthe catalyst was filtered off
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe residue was purified with silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ef07032fc5d74c0cb86e96c9d1243175
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376536B1

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