Tetrahydrofuran → HCID 13620271, compound

Temperature

80 °C

A mixture of pentane-2,4-dione (10.01 g) and 1,1-dimethoxy-N,N-dimethylmethanamine (12.51 g) was stirred at 80° C. for 1 hr. Tetrahydrofuran (20 mL) was added to the reaction mixture, benzylhydrazine dihydrochloride (21.46 g) was added by small portions under ice-cooling, and the mixture was stirred at 60° C. for 30 min. The reaction mixture was allowed to cool to room temperature, ethyl acetate (100 mL) and water (100 mL) were added, and the separated aqueous layer was extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (20 mL) and dried over anhydrous magnesium sulfate. Insoluble material was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title to compound (13.53 g) as a colorless oil.

1. additionwas added by small portions under ice-
2. temperaturecooling
3. stirringthe mixture was stirred at 60° C. for 30 min
4. temperatureto cool to room temperature
5. extractionthe separated aqueous layer was extracted with ethyl acetate (50 mL×2)
6. washThe combined organic layers were washed with brine (20 mL)
7. dry with materialdried over anhydrous magnesium sulfate
8. customInsoluble material was removed by filtration
9. concentrationthe filtrate was concentrated under reduced pressure
10. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-08fd69171e894c6db65a2ef9a7a3b267

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933069B2