Pyridine → HCID 72579577, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension consisting of 1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-phenyl-ethanone (compound A, 955 g) in ethanol (8 L) is added pyridine (4 L) and hydroxylamine hydrochloride (610 g). The resulting mixture is heated at 100° C. for two hours and subsequently stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure to afford a residue that is dissolved in ethyl acetate. The solution is washed with 5% aqueous citric acid and brine. The organic layer is separated, is dried over anhydrous Na2SO4, and is concentrated under reduced pressure. The concentrate is triturated with pentane. The triturated solids are collected by filtration to afford the solid product (480 g.) The filtrate is concentrated under reduced pressure and that concentrate is triturated with pentane. The solids are collected by filtration to provide another crop of solid product (320 g), which afforded a total of 800 g of Compound B.

Provenance & Evidence