Water → HCID 22137375, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-hydroxy-benzyl)-N-(4-iodo-phenyl)-benzenesulfonamide (3.20 g, 6.88 mmol) in 16 mL dimethylformamide was added allyl alcohol (1.20 mL, 17.60 mmol), Pd(OAc)2 (0.094 g, 0.42 mmol), sodium bicarbonate (1.42 g, 16.9 mmol), and tetrabutylammonium chloride (1.95 g, 7.02 mmol). The reaction was stirred at 50° C. for 19 hr. The reaction mixture was cooled, water and ethyl acetate were added, and the mixture was filtered through diatomaceous earth. The aqueous layer was washed twice with ethyl acetate. The combined organic layers were dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (25% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 2.12 g (78%) of N-(4-hydroxy-benzyl)-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide.

Provenance & Evidence