Ethyl chloroacetate → 2-[2-(2-Ethoxy-phenoxy)-1-(2-pyridinyl)ethoxy]acetic acid ethyl ester

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Reaction Steps

A mixture of sodium hydride (50%, 9.79 g, 0.204 mole, washed with hexane) in tetrahydrofuran (THF) was prepared. α-[(2-Ethoxyphenoxy)methyl]-2-pyridinemethanol (52.96 g, 0.204 mole) in 175 ml of THF was added dropwise under nitrogen with stirring over 1/2 hr. Stirring was continued for 1 hr at room temperature. Ethyl chloroacetate (24.98 g, 0.204 mole) in THF was added dropwise over 10 min. The resulting solution was heated at reflux for 2 hr and stirred at room temperature (72 hr). THF was removed, and the residue partitioned between diethyl ether and water. Removal of diethyl ether gave 57.9 g (0.168 mole, 82.4% yield) of the desired 2-[2-(2-ethoxy-phenoxy)-1-(2-pyridinyl)ethoxy]acetic acid ethyl ester as an oil. This structure of the product was confirmed by NMR.

Provenance & Evidence