Sodium Chloride → Triethyl ethane-1,1,2-tricarboxylate

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Reaction Steps

Diethyl-2-carbethoxysuccinate (formula 3, in which R are ethyl groups) is prepared by dissolving ethyl malonate (66 g, 0.5 moles) in tetrahydrofuran (500 ml). Sodium hydride (19.7 g of a 66% suspension in oil) (0.5 mole) is washed twice with petroleum ether (b.p. 30°-66°) and added to the stirred solution in small portions. Ethyl bromoacetate (83.5 g, 0.5 moles) is then added slowly from a dropping funnel. After stirring for 16 hours, the resultant white suspension is transferred to a separatory funnel along with a saturated aqueous sodium chloride solution (1 liter) and dichloroethane (1 liter). After shaking and separating the layers, the water layer is extracted with two additional liter portions of dichloroethane. The combined organic layers are dried over sodium sulfate before filtration and evaporation. The crude product is distilled under reduced pressure and the fractions boiling at 105°-112° at 2.5 mm Hg (12 ml) and 112°-115° (25 ml) are kept for use in the reaction of the next example.

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