Hydrochloric Acid → HCID 66618938, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium solution was added dropwise to a stirred suspension of 6-methylnicotinic acid (137 mg, 1.0 mmol) in THF (3 mL) over 30 min at −74° C. After 1 h a solution of 4-chloromethyl-5-methyl-3-phenyl-isoxazole (208 mg, 1.0 mmol) in THF (3 mL) was added dropwise such that the temperature did not exceed −68° C. The reaction mixture was stirred at −74° C. for 1 h, then HCl (1 N, 10 mL) added and the reaction mixture warmed to room temperature and extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 9:1) afforded the title compound (20 mg, 6%) as a light yellow oil. MS: m/e=168.3 [M+H]+.

Provenance & Evidence