Acetone → (3-Formyl-4-methoxy-phenyl)-cyanamide

Participants

Reaction Steps

To a solution of 1-(3-[1,3]-dioxolan-2-yl-4-methoxy-phenyl)-1H-tetrazole (0.46 g) in tetrahydrofuran (10 ml) at 0° under nitrogen n-butyl lithium (1.7 ml; a 1.6M solution in hexane) was added. After stirring for 5 min dilute aqueous hydrogen chloride solution (5 ml) and acetone (2 ml) were added. The mixture was stirred for 1 h before addition of dichloromethane (30 ml) and 8% aqueous sodium bicarbonate solution (20 ml). The layers were separated and the aqueous layer extracted with dichloromethane (3×30 ml). The organic layers ware combined, dried (Na2SO4), and evaporated to leave an orange solid. The material was washed with a small amount of ether and cyclohexane and dried in vacuo to yield the title compound as an orange solid (0.31 g). T.l.c.(5% Methanol/methyl tert-butyl ether), Rf 0.6.

Provenance & Evidence