Carbon Dioxide → HCID 67121019, compound

Participants

Reaction Conditions

Reaction Steps

957 mg (7.185 mmol) of 1,2,3,4-tetrahydroquinoline was dissolved in 10 ml of THF, and stirred at −78° C. for 30 minutes. 2.87 ml (7.185 mmol) of nBuLi was added thereto using a syringe under a nitrogen atmosphere (yellow suspension). The mixture was sufficiently stirred for 3 hours, and the temperature was increased to −20° C. to eliminate the gas. The temperature was cooled again to −78° C. and CO2 was injected to the mixture (The color of the mixture turned to colorless white). The temperature was increased to −20° C. and the remaining CO2 was eliminated in vacuum for 1 hour. Then, 5.07 ml (8.622 mmol) of tert-butyllitium (BuLi) was added to the mixture (The color of the mixture turned to red). While the temperature was maintained at −20° C., the mixture was sufficiently stirred for 2 hours, and 26.1 ml (8.622 mmol) of 0.33 M CeCl3.2LiCl solution dissolved in THF and 1.182 g (8.622 mmol) of tetramethyl cyclopentenone were added to the mixture under a nitrogen atmosphere. While the temperature was gradually increased to room temperature, the solvents were eliminated by venting. Then, the mixture was titurated using pentane under a nitrogen atmosphere and filtered to obtain a white crystalline powder (41%).

Provenance & Evidence