Hydrochloric Acid → HCID 86673324, compound

Temperature

105 °C

3-Furfural (0.96 g, 10 mmol) was dissolved in toluene (10 mL), N,N′-dimethylethylenediamine (1.08 mL, 10.0 mmol) and p-toluenesulfonic acid monohydrate (10 mg, 0.11 mmol) were added, and the mixture was stirred at 105° C. overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and 5% aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (20 mL), 1.54N n-butyllithium/hexane solution (3 mL) was added dropwise at −78° C., and the mixture was stirred for 1 hour. Dry ice was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hour. The solvent was evaporated under reduced pressure, N,N-dimethylformamide (10 mL), potassium carbonate (0.55 g, 4.0 mmol), and benzyl bromide (2.04 g, 11.9 mmol) were added to the obtained residue, and the mixture was stirred at 60° C. overnight. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (0.33 g).

1. customThe solvent was evaporated under reduced pressure
2. customthe residue was partitioned between ethyl acetate and 5% aqueous sodium hydrogen carbonate solution
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. customthe solvent was evaporated under reduced pressure
6. dissolutionThe obtained residue was dissolved in tetrahydrofuran (20 mL)
7. addition1.54N n-butyllithium/hexane solution (3 mL) was added dropwise at −78° C.
8. stirringthe mixture was stirred for 1 hour
9. additionDry ice was added to the reaction mixture
10. stirringthe mixture was stirred at room temperature for 2 hour
11. additionwere added to the obtained residue
12. stirringthe mixture was stirred at 60° C. overnight
13. extractionthe mixture was extracted with ethyl acetate
14. washThe extract was washed with saturated brine
15. dry with materialdried over anhydrous sodium sulfate
16. concentrationconcentrated under reduced pressure
17. customThe obtained residue was purified by silica gel column chromatography

ORD record

ord-ae7c8fd97b764d369434769e4d17edc2

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877805B2