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

HRID 1870513Notes

Reaction equation

HRID 1870513 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-526d5780fd2f49809b65e85c4e8b827c
Source dataset
uspto-grants-2000_08
Patent number
US06096780

Reaction notes

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