Hydrochloric Acid → HCID 22492686, compound

Participants

Reaction Conditions

Reaction Steps

In a 5 liter-three necked flask, 21.8 g (311 mM) of 1-pentene and 170 ml of THF were placed for dissolution, and under stirring in a nitrogen gas stream atmosphere, 673.4 ml of 0.5M-THF solution of 9-BBN(9-borabicyclo[3.3.1]nonane) was added dropwise at −25 to −20° C. over 15 minutes, followed by stirring for 1 hour at −10° C. and further for 3 hours at 5° C. Under stirring on an ice bath, to the reaction mixture, 6.75 g (5.84 mM) of Pd (PPh3)4 was added, and a solution of 79.6 g (287 mM) of 6-trifluoromethylsulfonyloxyquinoline in 1010 ml of DMF (methylformamide) was added dropwise, followed by the addition of 62.1 g of anhydrous potassium carbonate and then stirring for 10 minutes. The system was warmed and stirred at 50-54° C. for 3 hours. After the reaction, the reaction mixture was left standing for cooling and gradually poured into 3 liters of cool water, followed by extraction four times with 500 ml of toluene and washing of the organic layer with water. The organic layer was evaporated or condensed into ca. 1 liter thereof, followed by the addition of HCl so as to provide pH=1 and washing of the water layer (phase) with toluene. The water layer was alkalinized with 10% NaOH to pH=11 and extracted with toluene. The organic layer was dried and evaporated into a black liquid. The black liquid was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1) to obtain 42.6 g (yield: 74.4%) of 6-pentylquinoline.

Provenance & Evidence