Pyridine → HCID 21082446, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of titanium tetrachloride (22 mL, 0.2 mol), carbon tetrachloride (50 mL) and tetrahydrofuran (400 mL) at 0° C. is added benzophenone (18.2 g, 0.1 mol) and dimethyl malonate (13.3 g, 0.1 mol). After stirring at 0° C. for forty minutes, a solution of pyridine (32 mL) in tetrahydrofuran (70 mL) is added dropwise. The mixture is allowed to warm to room temperature and is then stirred for four days. The formation of a heavy precipitate requires the addition of more tetrahydrofuran to facilitate stirring. Water (100 mL) and ethyl acetate (100 mL) are then added. The mixtures separates into two layers. The aqueous layer is extracted with additional ethyl acetate. The combined organic layers are washed with brine, sodium bicarbonate and more brine. The solution is then dried over anhydrous magnesium sulfate and concentrated. The crude material is a white semi-solid slurry which is then recrystallized twice from heptane/ethyl acetate to afford 11.3 g of the title compound as a white solid melting at 120–122° C.

Provenance & Evidence