Sodium hydride → HCID 5151136, compound

Temperature

50 °C

Acetamide oxime (7.5 g), molecular sieves (4A) (10 g) and sodium hydride (5 g) were added to tetrahydrofuran (200 ml) and the mixture was refluxed under heating. To this reaction mixture was added dropwise ethyl 2-(methoxymethyloxy)cinnamate (12 g) and the mixture was continuously heated for 2 hr. After cooling, the mixture was poured on ice and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. Thereto were added tetrahydrofuran (10 ml) and 6N hydrochloric acid (20 ml) and the mixture was stirred with heating at 50° C. for 30 min to allow precipitation of crystals. The crystals were collected by filtration and dried to give the title compound (6.0 g) as white crystals, melting point 184-186° C.

1. temperaturethe mixture was refluxed
2. temperatureunder heating
3. temperaturethe mixture was continuously heated for 2 hr
4. temperatureAfter cooling
5. additionthe mixture was poured on ice
6. extractionextracted with ethyl acetate
7. concentrationThe organic layer was concentrated under reduced pressure
8. additionThereto were added tetrahydrofuran (10 ml) and 6N hydrochloric acid (20 ml)
9. customprecipitation of crystals
10. filtrationThe crystals were collected by filtration
11. customdried

ORD record

ord-8867c285e4234126b6f96c1698b49db3

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06720320B2