Triethylamine → HCID 14100418, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 15.4 g (66 mmol) of 2-(2-methyl-1-oxopropyl)-3-(2-pyridinyl)propenoic acid, methyl ester, 6.5 ml (46.2 mmol) of triethylamine and 8.2 g (66 mmol) of 4-fluorobenzaldehyde was added 15 mole percent of 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium chloride (Aldrich Chemical Co., Milwaukee, WI, USA). The resulting mixture was heated at 70° C. for 3 hours, cooled, dissolved in ethyl acetate and washed successively with brine and water. The organic layer was separated, dried to yield the crude products an oil. The material was redissolved in 300 ml of tetrahydrofuran, and 150 ml of water and 6.6 g (165 mmol) of sodium hydroxide were added. This mixture was vigorously stirred overnight, concentrated, and the residue dissolved in a mixture of diethyl ether and ethyl acetate. The extract was washed with water and then extracted with 2M hydrochloric acid. The acid extract was made alkaline and extracted with diethyl ether. The ether extract was evaporated to yield 7.2 g (36%) of 1-(4-fluorophenyl)-5-methyl-2-(2-pyridinyl)hexane-1,4-dione.

Provenance & Evidence