Tetrahydrofuran → Benzophenone

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of 1-(3-cyanobenzyl)-4-(2-methoxyphenyl)piperazine (16.5 g, 53.7 mmol) in 800 mL of tetrahydrofuran was added a solution of phenylmagnesium bromide in ethyl ether (53.6 mL, 3.0M) under nitrogen. The solution was slowly warmed to 25° C. and then brought to reflux. After 8 h of reflux, the reaction mixture was subsequently cooled to 0° C., and ice cold 6N HCl solution (650 mL) was added. The reaction mixture was then stirred at ambient temperature for 8 h. After cooling, the reaction mixture was poured into a separatory funnel and washed with ether. The aqueous layer was then basified with K2CO3 and then extracted with chloroform. The organic extracts were combined, dried (Na2SO4), and concentrated to provide a dark brown oil. This material was purified on a Waters Delta Prep 3000 LC apparatus (10% hexaneschloroform) to afford 19.4 g (93%) of desired benzophenone as a brown oil whose 1H NMR in CDCl3 was consistent with the desired structure.

Provenance & Evidence