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

Participants

Reaction Conditions

Reaction Steps

A solution of m-nitrophenol (1.8 g, 13 mmol) in dichloromethane (13 mL) was treated with dihydropyran (1.7 mL, 19 mmol) followed by pyridinium p-toluenesulfonate (0.32 g, 1.2 mmol) and stirred at 25° C. for 16 h. The reaction mixture was diluted with dichloromethane and washed with 1:1 brine/water (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to give a crude oil. This material was purified by flash column chromatography to give the desired product (2.5 g, 88%) as a clear oil.

Provenance & Evidence