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

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Reaction Steps

Combine 2-bromoethanol (14.2 mL, 200 mmol) and dihydropyrane (18.25 mL, 200 mmol) in dichloromethane (20 mL). Add Pyridinium p-toluenesulfonic acid (5 g, 20 mmol). After 2.5 hours, dilute the reaction mixture with diethyl ether and extract with water, 1/1 water/brine, water, and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Distill the residue to give the title compound: bp; 80-90° C. at 15-20 mm Hg.

Provenance & Evidence