Dimethyl Carbonate → Methyl 2-(3-cyanopyridin-4-YL)acetate

Participants

Reaction Conditions

Reaction Steps

2.52 g of 4-methyl-nicotinonitrile was dissolved in 15 mL of anhydrous THF and dropwisely added with 45 mL of 1M LHMDS at −78° C. and stirred for about 1 hour. At the temperature the above mixture was dropwisely added with 1.98 mL of dimethylcarbonate, stirred for about 1 hour. The mixture was then heated to 0° C. and stirred further for about 2 hours. The above mixture was added with 5 mL of saturated solution of ammonium chloride, diluted with 300 mL ethylacetate. Then, the organic solvent layer was washed with water, and saturated solution of sodium chloride, dried with anhydrous sodium sulfate and filtered. The filtrate was concentreated under reduced pressure and a silica gel column chromatography was performed on the resulting residue by using a mixed eluant of ethylacetate and hexane, wherein ethylacetate and hexane are mixed in 1:3 volume ratio, and 3.21 g (85%) of (3-cyano-pyridine-4-yl)-acetic acid methyl ester was obtained in colorless oil.

Provenance & Evidence