1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → n-(Bis(4-methoxyphenyl)(phenyl)methyl)-4-ethynylbenzenesulfonamide

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Reaction Steps

To a stirring slurry of 4-ethynylbenzenesulfonamide (1.81 g, 10.0 mmol) and DMTr-Cl (4.07 g, 12.0 mmol) in DCM (100 mL) was added TEA (2.8 mL). The resulting solution was allowed to stir at room temperature for overnight. Silica gel (3 g) was added to the solution followed by rotary evaporation of solvent in vacuo. The sample was absorbed onto silica gel was then loaded onto a pre-equilibrated column (with 10% TEA in hexane). Flash chromatography using 0-30% EtOAc in hexane as the gradient eluents gave the product 5 as a yellow solid (4.8 g, 99%).

Provenance & Evidence