Nitrogen → [2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-phenyl]-phenyl-methanone

Participants

Reaction Steps

A solution of 2-(4-methoxy-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole (4.5 g, 21.9 mmoles), prepared as described in example 1, in dry ethyl ether (90 ml), under stirring and dry N2 at 0° C., was added with 2.5M n-butyl lithium (9.6 ml, 24.1 mmoles) in hexane, and the reaction went on for 4 hours. In another flask a suspension of ZnCl2 (4.48 g, 33 mmoles) in dry ethyl ether (60 ml) was prepared and dropwise added with the solution of the lithium derivative at 0° C. and, after 1 hour, with benzoyl chloride (3.24 g, 23.02 mmoles). The mixture was left at room temperature for 3 hours, then added with bis(triphenylphosphine)palladium chloride (280 mg) and, after 3 days, poured into water/ice and extracted with ethyl acetate. The organic phases were washed with water, anhydrified and brought to dryness to give 3.5 g of the title compound (yield: 52%).

Provenance & Evidence