Dimethylformamide → Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(prop-1-yn-1-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyl-oxy)benzoate (Intermediate 123, 0.2 g), propyne (0.174 g), copper (I) iodide (0.008 g) and bis-(triphenylphosphine)palladium(II) chloride (0.029 g) were added to a solution of diisopropylamine (0.168 g) in DMF (2 ml) in a microwave vial. The mixture was degassed with argon and then heated in the microwave at 100° C. for 1 hour. After cooling, saturated aqueous ammonium chloride solution and ethyl acetate were added. The organic layer was separated, washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 7-25%. The resultant yellow gum was triturated with diethyl ether and the solid was collected by filtration to give methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(prop-1-yn-1-yl)benzoate (0.057 g) as a white solid.

Provenance & Evidence