3-Hydroxypyridine → HCID 15635484, compound

Participants

Reaction Steps

Sodium hydride (5.55 g, 139 mmol) was washed with hexane and then mixed with dimethoxyethane (200 ml). To the resulting mixture, 3-hydroxypyridine (12.0 g, 126 mmol) was added over 10 minutes under ice cooling. After stirring for 10 minutes, 2-(trimethylsilyl)ethoxymethyl chloride (25.2 g, 151 mmol) was added over 25 minutes under ice cooling. After stirring at room temperature for 14.5 hours, the reaction mixture was diluted with water under ice cooling and extracted with ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=67:33) to give 3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (23.9 g, 84%) as a brown oil.

Provenance & Evidence