Carbon Dioxide → [5-(4-chlorophenyl)pyridin-2-yl]propynoic Acid

Participants

Reaction Conditions

Reaction Steps

1.6 mL (2.46 mmol) of butyllithium solution (1.6M in hexane) are added dropwise at −10° C. to a solution of 0.5 g (2.34 mmol) of 5-(4-chlorophenyl)-2-ethynylpyridine in 30 mL of absolute THF and the mixture is stirred for five minutes at −8° C. stirred. The reaction mixture is combined with dry ice batchwise at −70° C., stirred for 1 hour at ambient temperature, and evaporated down. The residue is suspended in 5 mL of water and combined with 1.6 mL of 1N hydrochloric acid, whereupon a precipitate is formed. Then ethyl acetate is added and the suspension is filtered. The solid is dried in the vacuum drying chamber at 70° C. Yield: 0.25 g (41.5% of theory); melting point: 210° C.; C14H8ClNO2 (M=257.67); calc.: molecular ion peak (M+H)+: 258/260; found: molecular ion peak (M+H)+: 258/260.

Provenance & Evidence