Water → N-(2-chloro-4-hydroxy-benzyl)-2,4,6-trimethyl-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2-chloro-4-hydroxy-benzyl)-N-(4-iodo-phenyl)-2,4,6-trimethyl-benzenesulfonamide (0.652 g, 1.20 mmol) in 6 mL dimethylformamide was added allyl alcohol (0.204 mL, 3.01 mmol), Pd(OAc)2, sodium bicarbonate (0.253 g, 3.01 mmol), and tetrabutylammonium chloride (0.333 g, 1.20 mmol). The reaction mixture was stirred at 50° C. for 6 hr. and at room temperature overnight. Additional allyl alcohol (0.100 mL, 1.47 mmol), was added and the reaction mixture was stirred at 50° C. for an additional 4 hr. The reaction mixture was allowed to cool, water and ethyl acetate were added, and the mixture was filtered through diatomaceous earth. The filtrate was washed several times with water and the combined aqueous layers were extracted with ethyl acetate. The combined organic layers were dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography of the residue (2:1 hexanes:ethyl acetate) afforded 0.52 g (92%) of the title compound.

Provenance & Evidence