3,4-dihydro-2H-pyran → 4-Chloro-2-nitro-1-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzene

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A magnetically stirred solution of 4-chloro-2-nitrobenzyl alcohol (25.0 g, 133 mmol) and 3,4-dihydro-2H-pyran (118.2 mL, 16.8 g, 200 mol) in anhydrous dichloromethane (250 mL) was treated at 25° C. with pyridinium (toluenesulfonate (PPTS, 50 mg). The solution was stirred for 12 h, washed with 1 N NaOH (250 mL), brine (250 mL), dried (K2CO3), filtered, and concentrated in vacuo. Silica gel chromatography (4:1 hexane:ethyl acetate) of the concentrate gave 22.5 g (62%) of the title compound as an oil.

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