Triethylamine → HCID 69652716, compound

Participants

Reaction Steps

Dissolve 3,5-dichloropyridine-2-carboxaldehyde oxime (0.70 g, 0.0037 mol) in N,N-dimethylformamide (10 mL). Add N-chlorosuccinimide (0.55 g, 0.004 mol) in small portions and sitr at ambient temperature until reaction is complete. Pour the mixture into water and extract with ethyl acetate. Wash with water and dry over sodium sulfate. Concentrate in vacuo and use without further purification. Combine this material with ethyl-2-butynoate (6.0 mL, 0.052 mol) under a nitrogen atmosphere. Add triethylamine (3.29 mL, 0.024 mol) in diethyl ether (10 mL) in a dropwise manner and stir overnight at ambient temperature. Quench with water and extract with ethyl acetate. Concentrate and elute over silica gel with dichloromethane to give the desired isoxazole (0.43 g, 39%).

Provenance & Evidence