Triethylamine → HCID 16070660, compound

Participants

Reaction Steps

After adding 3-ethyl-3-hydroxymethyloxetane (465 g (4.0 mol)), triethylamine (486 g (4.8 mol)) and toluene (1,840 ml) to a glass flask having an inner volume of 5,000 ml equipped with a stirrer, a thermometer and a dropping funnel, while keeping the liquid temperature at 5-10° C., methanesulfonyl chloride (504 g (4.4 mol)) was gradually added to react at the same temperature for 3 hours and at room temperature for 3 hours with stirring. After the completion of the reaction, an aqueous saturated sodium bicarbonate solution (930 ml) was added to the reaction solution and a liquid separation was performed. Subsequently an aqueous layer was extracted with toluene (930 ml), an extract was combined with a previously extracted organic layer, and the combined liquid was washed with water (465 ml). A resultant organic layer was concentrated under reduced pressure to give, as a brown liquid, 3-ethyl-3-methanesulfonyloxymethyloxetane (777 g) having a purity of 95% (a value measured by 1H-NMR) (an isolated yield based on 3-ethyl-3-hydroxymethyloxetane: 95%).

Provenance & Evidence