(2-Chlorophenyl)-(4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)-methanol → (2-Chlorophenyl)-(4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)-methanone

Participants

Reaction Steps

To a solution of (2-chlorophenyl)-(4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)-methanol (8.6 g, 25.6 mmol) in toluene (300 mL) was added manganese (IV) oxide (Aldrich) (22.3 g, 10 eq), and the resulting mixture was heated to reflux with stirring for a total of 5 hours. The reaction was cooled to room temperature and then filtered through a 3.5 cm pad of Celite and the filtrate was concentrated to give 8.84 g of a crude product. Purification by Flash Column Chromatography on Silica Gel eluting with a gradient starting with pure hexanes and progressing to 2% ethyl acetate in hexanes and finally 5% ethyl acetate in hexanes gave the title compound as an off-white powder (1.388 g, (M+H)+=333).

Provenance & Evidence