Hydrochloric Acid → 1-(2-Benzyl-4-pyridyl)-4-methyl-1-pentanone

Participants

Reaction Steps

Anhydrous Et2O (15 mL) was added to magnesium turnings (0.310 g, 12.8 mmol) in a flame-dried flask. Addition of one drop of dibromoethylene was followed by slow addition of 1-bromo-3-methylbutane (1.619 g, 10.7 mmol) in 10 mL of anhydrous Et2O at a rate that kept the reaction mixture under reflux. Once the addition was completed the reaction was refluxed for 1 h and cooled to RT. The mixture was then added via cannula to a solution of 2-benzyl-4-cyanopyridine (1.000 g, 5.1 mmol) in 15 mL of anhydrous Et2O at 0° C. The mixture was stirred at RT for 30 min. and then refluxed for 3 h. The solution was cooled down to RT, poured into 200 mL of 0.5M HCl, and stirred for 30 min. A solution of 1M NaOH was added dropwise until the solution reached pH 9 and the resulting mixture was then extracted with ether (×3), dried with Na2SO4 and concentrated under vacuum. The resulting dark oil was purified by flash chromatography using 1:4 EtOAc/Hexane to give a brown oil (0.801 g, 58%)

Provenance & Evidence