Sodium Methoxide → 3-[(Oxiran-2-yl)methyl]-2-(propan-2-yl)-1,3-oxazolidine

Participants

Reaction Steps

3-(3-Chloro-2-hydroxypropyl)-2-isopropyl-1,3-oxazolidine (621 g., 3.0 mole) is charged into a 2-liter, three-necked flask equipped with a mechanical stirrer, thermometer and a dropping funnel. The flask is cooled to 0°-5° C. and 628 g. (2.91 moles) of sodium methoxide (25% solution in methanol) is added dropwise over a period of 31/2 hours, the clear solution becoming cloudy upon addition of the first several drops. Stirring is continued for an additional two hours after addition is completed. The solution is allowed to warm to room temperature and the sodium chloride is filtered off. The filtrate is concentrated on an evaporating rotary at 40° C/20 mm. Hg and the residue is refiltered to remove the remaining sodium chloride. The solution is then stripped at 40° C/20 mm. Hg until solvent is no longer removed. The resulting pale yellow liquid weighing 520 g. (98% yield) is wiping-film distilled at 100° C/0.5 mm. Hg to produce 368 g. (71% yield) of 3-(glycidyl)-2-isopropyl-1,3-oxazolidine in the form of a colorless mobile liquid.

Provenance & Evidence