3,4-dihydro-2H-pyran → 2-((4-Nitrobenzyl)oxy)tetrahydro-2H-pyran

Participants

Reaction Steps

A solution of 5.9 g (38.7 mmol) of 4-nitrobenzyl alcohol, 17.6 ml(193.5 mmol) of 3,4-dihydro-2H-pyran and 500 mg (2.6 mmol) of p-toluene sulfonic acid monohydrate in 200 ml of dichloromethane was stirred at room temperature for 4 hours. The reaction mixture was evaporated and the residue purified by flash chromatography on silica gel, using 1:4 ethyl acetate/hexane as eluent. Product containing fractions were combined and evaporated to give 8.52 g (93%) of 2-(4-nitrobenzyloxy)-tetrahydropyran as a pale yellow oil.

Provenance & Evidence