N-(3-fluoro-2-(hydroxymethyl)phenyl)pivalamide → N-(3-fluoro-2-formylphenyl)pivalamide

Participants

Reaction Steps

Pyridinium chlorochromate (596 mg, 2.76 mmol) was added to a solution of N-(3-fluoro-2-(hydroxymethyl) phenyl)pivalamide (415 mg, 1.84 mmol) in CH2Cl2 (50 mL) at 0° C. 5 min later the mixture was allowed stirring at room temperature for 3 hrs. The reaction mixture was passed through a thin pad layer of silica gel with CH2Cl2(2×50 mL), concentrated on rotary vacuum, and purified on a flash chromatography column eluting with 20˜50% EtOAc/hexanes (600 mL) to afford the expected product, N-(3-fluoro-2-formylphenyl)pivalamide, as a white solid (396 mg, 46% yield after five steps); 1H NMR (400 MHz, CDCl3) δ ppm 1.33 (s, 9 H), 6.76-6.83 (m, 1 H), 7.54 (td, J=8.44, 6.55 Hz, 1 H), 8.56 (d, J=8.56 Hz, 1 H), 10.38 (s, 1 H), 11.57 (s, 1 H); Mass spec. 224.11 (MH+), Calc. for C12H14FNO2 223.1.

Provenance & Evidence