Sodium Iodide → Propanedioic acid, (4-azidobutyl)[3-(3-pyridinyl)propyl]-, diethyl ester

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Reaction Steps

To a solution of 63.34 g (0.23 mole) of diethyl [3-(3-pyridyl)propyl]-malonate in 1.1 l dimethylformamide is added in small portions 9.91 g (0.25 mole) of sodium hydride as a 60% dispersion in oil. After stirring at room temperature for 0.5 h, 28 ml (0.23 mole) of 1-bromo-4-chlorobutane is added and then heated to 60° for 10 h. Then 68.26 g (0.46 mole) sodium iodide is added followed by 44.44 g (0.68 mole) sodium azide and 9.0 g crown ether 18-Crown-6. The reaction mixture is heated for 15 h at 60°, is then cooled and poured on ice. The mixture is then extracted with ether (4×500 ml). Combined organic extracts are extracted with 1N hydrochloric acid (1×200 ml, 2×100 ml). Combined aqueous extract is adjusted to pH 8 by addition of solid sodium bicarbonate and then extracted with ether (3×300 ml). Combined organic extracts are washed with water (3×100 ml), brine (1×300 ml), dried (MgSO4), filtered and evaporated to dryness to give diethyl [4-azidobutyl][3-(3-pyridyl)propyl]-malonate as an oil.

Provenance & Evidence