Triethylamine → Dimethyl 2,2-dinitropropylmalonate

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Triethylamine was added dropwise to a solution of 1.4 g (0.010 mol) of dimethyl methylenemalonate and 1.6 g (0.0133 mol) of 1,1-dinitroethane in 15 ml of ether at 0°, until yellow coloration persisted in the solution. The solution was allowed to stand 1 hr at ambient temperature and was then washed with 10% sodium bicarbonate, 1 N hydrochloric acid and water. The solution was dried over sodium sulfate, and the solvent was removed under vacuum. Column chromatography on a 100 g column of silica gel (CCl4 --CH2Cl2) and recrystallization of the product (methylene chloride-hexane, -78°) gave 1.9 g (72%) of dimethyl 2,2-dinitropropylmalonate, a white crystalline solid, mp 44°: NMR (CDCl3) 3.75 (s, 6 H, CH3), 3.1-3.5 (m, 3 H, CHCH2) and 2.13 (s, 3 H, C--CH3); IR (neat) 1730 (C=O) and 1570 cm-1 (NO2).

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