Hydrochloric Acid → 6-Cyano-2-octyl-2-methyl-1-indanone

Participants

Reaction Conditions

Reaction Steps

In a 2 liter-reaction vessel, 1.6 g (1.15×10-1M) of diisopropylamine and 450 ml of dry THF were placed and cooled to -10 ° C. Under stirring, 72.8 ml (1.5 M) of a solution of n-butyllithium in hexane was added dropwise to the above mixture in 10 minutes and cooled to -70° C. A solution of 28.0g (1.04×10-1M) of 6-cyano-2-octyl-indanone in 150 ml of dry THF was then added dropwise in 30 minutes, followed by stirring for 2 hours while the reaction temperature was gradually restored to room temperature. After the reaction, the reaction mixture was cooled to -20° C., and 28.0 g (1.97×10-1M) of methyl iodide was added dropwise thereto in 10 minutes. After the addition, the resultant mixture was stirred for 18 hours while the reaction temperature was gradually restored to room temperature. After the reaction, 1N-HCl was added dropwise to the reaction mixture under cooling to decompose the reaction mixture. The organic layer was successively washed with water, sodium hydrogencarbonate and water, followed by drying with anhydrous magnesium sulfate and distilling-off of the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: chloroform/n-hexane=1/1; 300 mesh silica gel: 50 times in weight) to obtain 15.2 g of 6-cyano-2-octyl-2-methyl-1-indanone (Yield: 52%).

Provenance & Evidence