Water → 5-(4-Chlorobutyl)-3-(1-methylethyl)-2-oxazolidinone

Participants

Reaction Steps

A solution of phosgene (287 mL of a 20% solution, 273 g, 0.55 mol) in toluene and additional toluene (100 mL) was cooled to -10° C. by an ice/methanol bath and a solution of tetrahydro-N-(1-methylethyl)-2H-pyran-2-methanamine (41.13 g, 0.262 mol) and triethylamine (27.9 g, 0.276 mol) in toluene (300 mL) was added dropwise, keeping the temperature below 5° C. The mixture was warmed to room temperature and refluxed under nitrogen for 30 min. Zinc chloride (0.65 g) was added and refluxing was continued for 15 min. An additional portion of zinc chloride (0.32 g) was added, and the mixture was refluxed for 24 hr and allowed to stand at room temperature for several days. Water (750 mL) was added, and the layers were separated. The organic layer was washed twice again with water and once with a saturated sodium chloride solution, dried (magnesium sulfate), treated with charcoal, filtered, and evaporated to an oil. The oil was distilled under reduced pressure, and the fraction distilling from 148°-165° C./0.3 mm was collected to give 46.7 g (81% yield).

Provenance & Evidence