1,3-Diethyl 2-oxopropanedioate → HCID 178470247, compound

To a suspension of butane-1,2-diamine hydrochloride (6.40 g, 39.7 mmol) in ethanol (60 mL) was added diisopropylethylamine (14 mL, 80.4 mmol), and the mixture was stirred at room temperature for 10 min. To this solution was added dropwise diethyl ketomalonate (6 mL, 39.3 mmol) at 0° C., and the mixture was stirred at room temperature for 1.5 hr with heating under reflux for 20 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a small amount of ethanol. The solution was passed through silica gel (100 g, eluent, hexane:ethyl acetate=1:1→ethyl acetate). The eluate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1→ethyl acetate) to give the title compound (1.94 g, 25%) as a pale-yellow powder.

1. stirringthe mixture was stirred at room temperature for 1.5 hr
2. temperaturewith heating
3. temperatureunder reflux for 20 hr
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. dissolutionthe residue was dissolved in a small amount of ethanol
6. concentrationThe eluate was concentrated under reduced pressure
7. customthe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1→ethyl acetate)

ORD record

ord-0104018860c6421ebe7cdaf54b123496

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486965B2