Sodium Thiosulfate → 1-(3-(Methoxymethoxy)pyridin-4-yl)ethanone

Participants

Reaction Steps

Dess-Martin periodinane (18 g, 43 mmol) was added to a stirring mixture of 1-(3-(methoxymethoxy)pyridin-4-yl)ethanol (4.6 g, 25 mmol), NaHCO3 (6.3 g, 75 mmol), and CHCl3 (75 mL) at RT. After 24 h, 1.0 M aqueous Na2S2O3 was added, the reaction mixture was stirred for 90 min, partitioned between ethyl acetate and 1.0 M aqueous Na2S2O3, the layers were separated, the organic layer was washed with 1.0 M aqueous Na2S2O3, water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (gradient elution; 2:1→1:1 hexane-ethyl acetate) to give 3.9 g (86%) of 1-(3-(methoxymethoxy)pyridin-4-yl)ethanone as a clear yellow-orange oil.

Provenance & Evidence