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

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.

1. customequipped with a mechanical stirrer
2. temperatureThe flask is cooled to 0°-5° C.
3. additionupon addition of the first several drops
4. additionafter addition
5. filtrationthe sodium chloride is filtered off
6. concentrationThe filtrate is concentrated on an evaporating rotary at 40° C/20 mm. Hg
7. customto remove the remaining sodium chloride
8. customis then stripped at 40° C
9. customno longer removed
10. distillation(98% yield) is wiping-film distilled at 100° C/0.5 mm. Hg
11. customto produce 368 g

ORD record

ord-5fdff2754173465482b4791d34f1940f

Source dataset

uspto-grants-1977_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04002637