Potassium Carbonate → HCID 19744571, compound

Participants

Reaction Steps

The resulting vinyl pyridine (573 mg) was dissolved in 5 ml of methanol, and under ice cooling, 104 mg of sodium borohydride was added. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added to the residue. The organic layer was separated and evaporated under reduced pressure. The residue was dissolved in 5 ml of chloroform and under ice cooling, 0.17 ml of thionyl chloride was added. The mixture was stirred at room temperature for 1 hour. The reaction mixture was evaporated under reduced pressure, and the residue was treated with ethyl ether to give 412 mg (yield 57%) of (E)-2-2-(3-chloromethylphenyl)vinyl]pyridine hydrochloride as colorless needles having a melting point of 159° to 160° C. The resulting hydrochloride was dissolved in 5 ml of dimethylformamide, and 219 mg of (E)-N-methyl-6,6-di-methyl-2-hepten-4-ynylamine hydrochloride and 166 mg of potassium carbonate were added, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water and benzene. The organic layer was separated and evaporated, then the residue was purified by medium-pressure liquid chromatography [column: Lobar column, size B, Lichroprep Si 60 (a product of E. Merck Co.); eluting solvent: hexane/ethyl acetate=6/1→3/1] to give 277 mg (yield 67%) of the captioned compound as a colorless oil.

Provenance & Evidence