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

Participants

Reaction Steps

A solution of 8.5 g (35.9 mmol) of 2-(4-nitrobenzyloxy)-tetrahydropyran in 150 ml of methanol was hydrogenated at room temperature and atmospheric pressure in the presence of 800 mg of 10% palladium on carbon for 8 hours. The catalyst was removed by filtration and the filtrate evaporated to give a dark yellow oil. Purification by flash column chromatography on silica gel using 1:2 ethyl acetate/hexane as eluent gave 4.8 g (65%) of 4-(tetrahydropyran-2-yloxymethyl)aniline as a pale yellow oil. [Mass spectrum (ESI) [MH+MeCN]+ =249].

Provenance & Evidence