Chloroacetyl chloride → HCID 86708291, compound

Diethyl malonate (5.0 mL, 0.033 mol) was added dropwise to a solution of sodium hydride (60% w/w in oil, 2.7 g, 0.066 mol) in anhydrous tetrahydrofuran (50 mL) that cooled with ice bath. The mixture was refluxed for 5 min. The reaction mixture was cooled with ice bath, chloroacetyl chloride (2.8 mL, 0.035 mol) was added dropwise to the reaction mixture and the mixture was stirred for 1 h then stirred at 45° C. for 1 h. The reaction mixture was cooled with ice bath again then piperidine (3.9 mL, 0.040 mol) was added dropwise and stirred at ambient temperature for further 12 h. The reaction mixture was diluted with aqueous saturated sodium bicarbonate solution, and extracted with ethyl acetate for 2 times then extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel(chloroform/methanol) to afford ethyl 4-oxo-2-piperidino-4,5-dihydrofuran-3-carboxylate as solid (3.5 g, y. 45%).

1. temperaturecooled with ice bath
2. temperatureThe mixture was refluxed for 5 min
3. temperatureThe reaction mixture was cooled with ice bath
4. stirringthen stirred at 45° C. for 1 h
5. temperatureThe reaction mixture was cooled with ice bath again
6. stirringstirred at ambient temperature for further 12 h
7. extractionextracted with ethyl acetate for 2 times
8. extractionthen extracted with chloroform
9. washThe organic layer was washed with brine
10. dry with materialdried over sodium sulfate
11. concentrationconcentrated
12. customThe residue was purified by chromatography on silica gel(chloroform/methanol)

ORD record

ord-848c852a1521423b9bdaf8453274e37d

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742113B2