[4-(Tert-butyldimethylsilyloxymethyl)-phenyl]-pyridin-3-yl-methanol → [4-(tert-Butyldimethylsilyloxymethyl)-phenyl]-pyridin-3-yl-methanone

Participants

Reaction Conditions

Reaction Steps

Add manganese dioxide (1.44 g) to a stirred solution of [4-(tert-butyldimethylsilyloxymethyl)-phenyl]-pyridin-3-yl-methanol (360 mg, 0.303 mmol) in anhydrous 1,4-dioxane (25 mL). Heat the mixture to 70° C. overnight. Cool the reaction mixture to room temperature, filter through Celite® and wash with EtOAc. Concentrate the filtrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (1:1) to provide the desired intermediate (233 mg, 65%). GC-MS m/z: 327 (M+).

Provenance & Evidence