4,4-dimethyl-1-phenylpent-1-yn-3-one

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 1-[2-(4-chlorophenyl)-2-oxoethyl]-4-(pyridin-2-ylmethoxy)pyridinium bromide (750 mg, 1.79 mmol) and 4,4-dimethyl-1-phenylpent-1-yn-3-one (333 mg, 1.79 mmol) in DMF (10.0 mL) is added TEA (0.37 mL, 2.68 mmol). The mixture is stirred at 70° C. for 18 h then treated with DDQ (406 mg, 1.79 mmol) and stirred for an additional 1 h. The mixture is then cooled to 23° C. and partitioned between water and EtOAc. The organics are collected, dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, hexanes to 50% EtOAc in hexanes) gives the title compound (121 mg, 13%). stirred for an additional 1 h The mixture is then cooled to 23° C. partitioned between water and EtOAc The organics are collected dried with MgSO4 filtered concentrated in vacuo Purification of the crude by flash chromatography (SiO2, hexanes to 50% EtOAc in hexanes)