Heptyl-[2-(4-hydroxymethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester → [2-(4-Formyl-phenyl)-ethyl]-heptyl-carbamic acid tert-butyl ester

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Reaction Steps

To a stirred solution of heptyl-[2-(4-hydroxymethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (4.9 mmol, 1.7 g) in anhydrous ether (50 mL) was added activated manganese dioxide (Aldrich, 5 g). The resulting suspension was stirred at room temperature adding further 2 g portions of manganese dioxide every 2 hours until the starting material had been consumed as determined by TLC. The mixture was filtered through a Celite® plug and washed through exhaustively with dichloromethane. The yellow filtrate was concentrated to a yellow oil which was chromatographed on silica gel (20% ethyl acetate/hexanes) to give [2-(4-formyl-phenyl)-ethyl]-heptyl-carbamic acid tert-butyl ester as a clear oil (1.30 g, 76%).

Provenance & Evidence