18-Crown-6 → Methyl 6-fluoro-3-nitro-2-pyrazinecarboxylate

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Reaction Steps

In 2.0 mL of acetonitrile was dissolved 0.1 g of methyl 6-chloro-3-nitro-2-pyrazinecarboxylate. After adding 40 mg of potassium fluoride and 61 mg of 18-crown-6-ether successively, the mixture thus obtained was stirred at room temperature for 1.5 hours. Then, a mixture of 10 mL of ethyl acetate and 10 mL of water was added, pH was adjusted to 7.0 with saturated aqueous solution of sodium hydrogen carbonate, and the organic layer was separated. The organic layer thus obtained was washed with saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate=7:1] to obtain 0.03 g of methyl 6-fluoro-3-nitro-2-pyrazinecarboxylate as a light yellow-colored oily product.

Provenance & Evidence