N-(3-fluoro-2-(hydroxymethyl)phenyl)pivalamide → N-(3-fluoro-2-formylphenyl)pivalamide
Reaktionsgleichung
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][C:13]1[C:14]([CH2:26][OH:27])=[C:15]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:16]=[CH:17][CH:18]=1>C(Cl)Cl>[F:12][C:13]1[C:14]([CH:26]=[O:27])=[C:15]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:22])[CH3:23])[CH:16]=[CH:17][CH:18]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
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.