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

HRID 1387966Notes

Reaction equation

HRID 1387966 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-3f33c6a9a0ba453585c011c82c1eb442
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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