Acetonitrile → HCID 13020125, compound

Participants

Reaction Steps

A mixture of 6.5 g (0.16 mole) of acetonitrile and 50 ml of dry tetrahydrofuran (THF) was slowly added under N2 -atm to a mixture of 100 ml of 1.5 M n-butyllithium in hexane and 50 ml of dry THF at -50° C. After stirring for 35 minutes a solution of 36.5 g (0.14 mole) of 4-bromophenyl-3-pyridylketone in 250 ml of dry THF was added at -50° C. The temperature was kept at -70° C. for 15 minutes, then the reaction mixture became viscous and it was allowed to reach ambient temperature. The product was poured into a stirred mixture of 500 g of icewater and 500 ml of methylene chloride. The layers were separated and the aqueous layer was extracted with 2×200 ml of CH2Cl2. The combined organic layers were washed with water and dried. The solvent was evaporated giving 39.7 g of an oil. It was dissolved in 550 ml of hot i-PrOH and a solution of 35 ml of 4M HCl-ether (0.14 mole) in 100 ml of i-PrOH was added. After cooling there was collected 34.6 g (74%) of the hydrochloride of 3-(4-bromophenyl)-3-hydroxy-3-(3-pyridyl)-propionitrile. M.p. 158°-161° C. ##STR33##

Provenance & Evidence