Diethyl Malonate → HCID 178470508, compound

Sodium metal (3.8 g, 164 mmol) was added to absolute ethanol (200 mL). The mixture was stirred under reflux until a clear solution was obtained. Diethyl malonate (26.3 g, 164 mmol) was added to this solution which was again heated to reflux, and a solution of 1-(azidomethyl)-4-methoxybenzene (i.e. the product of Step A, 25.5 g, 156 mmol) in ethanol (50 mL) was added at once. The reaction mixture was stirred at reflux for 24 h then the reaction mixture was concentrated to dryness under reduced pressure. The residue was diluted with water (100 mL) and acidified to pH 2 with 1 M aqueous hydrochloric acid, stirred for 30 min, and the solid was filtered off and washed with water. The solid was dried over phosphorus pentoxide. The solid was stirred in chloroform (500 mL) and the insoluble solids were filtered off. Hexanes (400 mL) were added to precipitate the product, which was removed by filtration and dried to afford the title compound (12.0 g) as a beige solid.

1. temperatureunder reflux until a clear solution
2. customwas obtained
3. temperaturewas again heated
4. temperatureto reflux
5. stirringThe reaction mixture was stirred
6. temperatureat reflux for 24 h
7. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
8. additionThe residue was diluted with water (100 mL)
9. stirringstirred for 30 min
10. filtrationthe solid was filtered off
11. washwashed with water
12. dry with materialThe solid was dried over phosphorus pentoxide
13. stirringThe solid was stirred in chloroform (500 mL)
14. filtrationthe insoluble solids were filtered off
15. additionHexanes (400 mL) were added
16. customto precipitate the product, which
17. customwas removed by filtration
18. customdried

ORD record

ord-5847b5bb474f418886f0cc3081de8d95

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302999B2