[4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]methanol → 4-Nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-5-carbaldehyde

Participants

Reaction Steps

To a solution of [4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]methanol (7.776 g, 28.38 mmol) in chloroform (500 mL) was added manganese dioxide (29.18 g, 9 eq). The resulting mixture was heated at reflux for 4 hours, cooled to room temperature and stirred overnight. The reaction mixture was again heated to reflux for 3 hours, filtered through a 3 cm plug of celite using additional chloroform. The filtrate was concentrated to give 4.55 g of crude material and purified via silica gel chromatography with a 2-4% ethyl acetate in hexanes gradient to give the title compound as a colorless oil (1.55 g). M+=271

Provenance & Evidence