Methyl morpholine oxide → N-(2-fluoro-4-hexanoylphenyl)-2,2-dimethylpropanamide

Participants

Reaction Steps

A solution of N-[2-fluoro-4-(1-hydroxyhexyl)phenyl]-2,2-dimethylpropanamide (18.5 g, 62.6 mmol) in CH2Cl2 (300 mL) was treated with 4-methylmorpholine N-oxide (7.35 g, 62.6 mmol) followed by tetrapropylammonium perruthenate (TPAP, 0.22 g, 0.63 mmol). The mixture was stirred at room temperature for 30 minutes, then treated with additional TPAP (0.88 g, 2.5 mmol) and stirred an additional 30 minutes at room temperature. The mixture was filtered through a pad of MgSO4 atop a pad of silica gel, washing through with EtOAc (500 mL). The filtrate was evaporated under vacuum to afford N-(2-fluoro-4-hexanoylphenyl)-2,2-dimethylpropanamide (17.8 g, 97%) as a white solid.

Provenance & Evidence