Triacetoxyperiodinane → 1-(5-(Methoxymethoxy)-2-neopentylpyridin-4-yl)ethanone

Participants

Reaction Steps

To a solution of 1-(5-(methoxymethoxy)-2-neopentylpyridin-4-yl)ethanol (24.4 g, 96.3 mmol) and sodium bicarbonate (32.4 g, 385 mmol) in CHCl3 (500 mL) at 0° C. was added Dess-Martin Periodinane (53.1 g, 125 mmol). The reaction was stirred 5 h, quenched with saturated aqueous Na2SO3 (300 mL), extracted with CH2Cl2 (3×250 mL), the combined organic layers washed with saturated NaCl (300 mL), dried (Na2SO4), and concentrated to give a yellow oil. Purification by ISCO (330 g SiO2, 20% EtOAc/Hexane) gives 1-(5-(methoxymethoxy)-2-neopentylpyridin-4-yl)ethanone as a clear, colorless oil.

Provenance & Evidence