Triethylamine → HCID 57425441, compound

Participants

Reaction Steps

Dissolve 3-fluoropyridine-2-carboxaldehyde oxime (2.55 g, 0.018 mol) in N,N-dimethylformamide (20 mL). Add N-chlorosuccinimide (2.71 g, 0.02 mol) in small portions and stir for 6 h at ambient temperature. Pour into water and extracte with ethyl acetate. Wash the combined extracts with water and dry over sodium sulfate. Concentrate in vacuo to give crude product. Use without further purification. MS(FD): M+ 174.0, 175.9 m/z. Combine this material with ethyl-2-butynoate (5.30 mL, 0.046 mol) in diethyl ether (200 mL) under a nitrogen atmosphere. Add triethylamine (3.29 mL, 0.024 mol) in a dropwise manner and stir over a weekend at ambient temperature. Quench the mixture with water and extract with ethyl acetate. Dry the combined extracts over sodium sulfate and concentrate. Elute over silica gel with methanol/dichloromethane to give the desired isoxazole (0.52 g, 11%). ES(ES): (M+1)+ 251.0, 252.0 m/z.

Provenance & Evidence