3,4-dihydro-2H-pyran → 2-Chloro-5-{[(oxan-2-yl)oxy]methyl}pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 85 g of 6-chloro-3-pyridinecarbinol, 800 ml of dioxan and 129.8 g of 3,4-dihydro-2H-pyran was treated with 5.7 g of p-toluenesulphonic acid monohydrate, stirred at room temperature for 0.75 hours and subsequently at 65° C. for 2.75 hours. The reaction mixture was treated with 15 ml of triethylamine and, after cooling, taken up in diethyl ether. Repeated washing with saturated sodium chloride solution, drying over sodium sulphate and evaporation yielded 153.2 g of crude 2-chloro-5-[(tetrahydro-2-pyranyloxy)methyl]pyridine as a brown-red oil.

Provenance & Evidence