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

HRID 2228227Notes

Reaction equation

HRID 2228227 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

HCID 184721974-(2-Tetrahydropyranyloxymethyl)anilineYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0effa2d2615449bc8cebfb61da0d48cb
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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