Hydrochloric Acid → HCID 10624338, compound

Participants

Reaction Steps

In a dry flask was placed sodium hydride as a 60% suspension in oil (800 mg, 2.0 mmol). Most of the oil was removed by washing twice with hexanes. The remaining solid sodium hydride was then suspended in dry 1,2-dimethoxyethane (DME) (20 mL). A solution of dibenzyl malonate (5.0 mL, 2.0 mmol) in DME (15 mL) was then added dropwise with stirring. The mixture was stirred at room temperature for 0.5 hr after which a solution of 2-chloro-3-nitro-5-trifluoromethyl pyridine (2.3 g, 10.2 mmol) in DME (15 mL) was added. Stirring at room temperature was continued overnight and the reaction mixture was poured into ice/water. Following acidification to pH 3 with 1N HCl solution, the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to leave an oil. This was subjected to flash chromatography on silica gel using toluene as eluant. All fractions containing the desired product were combined and concentrated to leave a tan solid; 3.8 g (79%): mp 82°-84° C.

Provenance & Evidence