Triacetoxyperiodinane → 3-((Tert-butyldimethylsilyl)oxy)-2,2-dimethylpropanal

Participants

Reaction Steps

To a solution of 3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propan-1-ol (3.0 g, 13.8 mmol) in DCM (30 ml) was added Dess-Martin reagent (8.6 g, 20.6 mmol) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was then washed with water and concentrated in vacuo. The crude residue was purified by flash chromatography (eluted with petroleum ether:EtOAc=100:1) to afford the title compound (1.6 g, 54%): 1H NMR (CDCl3, 400 MHz) delta 0.05 (s, 6H), 0.88 (s, 9H), 1.17 (s, 6H), 3.59 (s, 2H).

Provenance & Evidence