To a solution of (tetrahydro-2H-pyran-4-yl)methanol (74.2 mg, 0.639 mmol) and methyl 5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate (500 mg, 1.277 mmol) in toluene (0.5 mL) at room temperature, was added a solution of 2-(tributylphosphoranylidene)acetonitrile (339 mg, 1.405 mmol) in toluene (0.5 mL) in one charge. The reaction mixture was stirred vigorously for 1 hour, then left to stand overnight. Additional 2-(tributylphosphoranylidene)acetonitrile (339 mg, 1.405 mmol) and (tetrahydro-2H-pyran-4-yl)methanol (74.2 mg, 0.639 mmol) were added and the reaction mixture stirred for an additional 8 hours. The solvent was evaporated in vacuo to give the crude product, which was purified by silica (Si) chromatography (0-100% ethyl acetate-cyclohexane) to give the title compound as an orange gum, 109.6 mg. LCMS [LCMS1] Rt 1.37 min, m/z (ES+) 490 (M+H).
