3,4-dihydro-2H-pyran → 2-[2-(2-Chloroethoxy)ethoxy]oxane

Participants

Reaction Conditions

Reaction Steps

In a drybox, 2-(2-chloroethoxy)ethanol (50.0 g, 0.401 moles) and 135 mL chloroform were added to a 500 mL 3-necked flask equipped with a stir bar, addition funnel and septum. 3,4-Dihydro-2H-pyran (39.7 g, 0.472 moles) in 35 mL chloroform was added dropwise over 30 min using an addition funnel. At the end of the addition, the flask was warm. The addition funnel was removed from the flask and replaced with a stopper, and the flask was transferred to the hood and placed under an atmosphere of nitrogen. Twelve drops of concentrated HCl were added dropwise via syringe. The septum was then replaced with a water condenser. The reaction was heated at 40° C. for 1 hr, and then allowed to cool to room temperature. The flask was opened to the air, 9 g of K2CO3 were added to the reaction mixture, and the mixture was stirred for two min before filtering. The solvent was removed via rotary evaporation, and the product was dried under vacuum for 8 hr at room temperature to give 84 g (0.406 moles) of 2[2-(2-chloroethoxy)ethoxyl]-tetrahydropyran.

Provenance & Evidence