2-(((Tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol → 2-({[tert-Butyl(dimethyl)silyl]oxy}methyl)prop-2-enal

Participants

Reaction Steps

To a solution of 2-(((tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol (Intermediate 157, 11.35 g, 56.09 mmol) in DCM (150 mL) was added manganese dioxide (activated, 5 g) (28.7 g, 280.43 mmol). The reaction mixture was stirred at room temperature for three days. More MnO2 was added and continued stirring until TLC shows minimum starting material. The reaction mixture was filtered through a pad of silica, evaporated at ˜15° C. and purified on silica gel column (5-20%, EA/Hex) to afford the title compound (6.70 g, 59.6%) as a colorless oil.

Provenance & Evidence