Water → HCID 22137280, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(3-hydroxy-benzyl)-N-(4-iodo-phenyl)-2,4,6-trimethyl-benzenesulfonamide (0.36 g, 0.71 mmol) in 3 mL dimethylformamide was added allyl alcohol (0.121 mL, 1.77 mmol), Pd(OAc)2, sodium bicarbonate (0.149 g, 1.77 mmol), and tetrabutylammonium chloride (0.197 g, 0.71 mmol). The reaction mixture was stirred at 50° C. for 24 hr. Additional allyl alcohol (0.121 mL, 1.77 mmol), Pd(OAc)2, sodium bicarbonate (0.060 g, 0.71 mmol), and tetrabutylammonium chloride (0.098 g, 0.36 mmol) were added and the reaction mixture was stirred at 50° C. for an additional 24 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 with water and the organic layer was dried (magnesium sulfate) and concentrated in vacuo. Medium pressure silica gel chromatography of the residue (3:1 hexanes:ethyl acetate) afforded 0.20 g (64%) of the title compound. MS 436.2 (M−1)+

Provenance & Evidence