Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 2-(oxetan-3-ylidene)acetate

To a solution of (carbethoxymethylene)triphenylphosphorane (1.95 Kg, 5.61 mol) in dichloromethane (4 L) at 0° C. was added over 1 hour, a solution of 3-oxetanone (400 g, 5.55 mol) in dichloromethane (2 L) maintaining the temperature below 10° C. The reaction was warmed gradually to room temperature and stirred for 1.5 hours. The reaction was warmed to 30° C. and dichloromethane (˜4 L) removed in vacuo. Heptane (5 L) was added and the mixture distilled under vacuum for a further 1 hour. Further heptane (2.5 L) was added, the temperature increased to 50° C. and the reaction continued to be distilled under vacuum for a further 2 hours. The mixture was cooled to 0° C. and aged for 1 hour at atmospheric pressure. The solid was collected by filtration and washed with heptane (2×2.5 L). The pale yellow filtrate was concentrated in vacuo to afford the title compound as a pale yellow mobile liquid (757 g, 96% yield).

1. temperatureThe reaction was warmed to 30° C.
2. customdichloromethane (˜4 L) removed in vacuo
3. additionHeptane (5 L) was added
4. distillationthe mixture distilled under vacuum for a further 1 hour
5. additionFurther heptane (2.5 L) was added
6. temperaturethe temperature increased to 50° C.
7. distillationto be distilled under vacuum for a further 2 hours
8. temperatureThe mixture was cooled to 0° C.
9. waitaged for 1 hour at atmospheric pressure
10. filtrationThe solid was collected by filtration
11. washwashed with heptane (2×2.5 L)
12. concentrationThe pale yellow filtrate was concentrated in vacuo

ORD record

ord-5ce237b775e14387a87c1d37b3243492

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079878B2