Triethylamine → HCID 67079022, compound

4-Benzyloxybenzaldehyde (5.0 g, 23.6 mmol) was dissolved in a mixture of ethanol (40 mL) and THF (10 mL), and sodium bicarbonate (2.4 g, 28.3 mmol) was then added to the solution. While stirring the mixture at room temperature, an aqueous solution (25 mL) of hydroxylamine hydrochloride (1.86 g, 25.9 mmol) was added thereto. The obtained mixture was stirred for 1.5 hours. The reaction solution was concentrated under reduced pressure, and water was then added to the residue, followed by extraction three times with ethyl acetate. The organic layer was washed with a saturated saline, and it was then dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was dissolved in dimethylformamide (40 mL), and N-chlorosuccinimide (3.15 g, 23.6 mmol) was then added to the solution. The obtained mixture was stirred at room temperature overnight. Thereafter, water was added to the reaction solution, and it was then extracted with ethyl acetate three times. The organic layer was washed with a saturated saline, and it was then dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified with a fractionation purification apparatus (Biotage, ethyl acetate:hexane=2:98-3:7). The obtained compound (3.0 g, 11.5 mmol) was dissolved in dichloroethane (30 mL), and 2-butyn-1-ol (2.6 mL, 34.4 mmol) and triethylamine (1.9 mL, 13.8 mmol) were then added to the solution. The obtained mixture was stirred at 90° C. for 4 hours. Thereafter, the reaction solution was concentrated under reduced pressure, and the residue was then purified with a fractionation purification apparatus (Biotage, ethyl acetate:hexane=1:4-4:1), so as to obtain the title compound (0.88 g, 26%) in the form of an isometric mixture.

1. additionwas then added to the solution
2. stirringThe obtained mixture was stirred for 1.5 hours
3. concentrationThe reaction solution was concentrated under reduced pressure, and water
4. additionwas then added to the residue
5. extractionfollowed by extraction three times with ethyl acetate
6. washThe organic layer was washed with a saturated saline, and it
7. dry with materialwas then dried over anhydrous sodium sulfate
8. concentrationfollowed by concentration under reduced pressure
9. dissolutionThe residue was dissolved in dimethylformamide (40 mL)
10. stirringThe obtained mixture was stirred at room temperature overnight
11. extractionwas then extracted with ethyl acetate three times
12. washThe organic layer was washed with a saturated saline, and it
13. dry with materialwas then dried over anhydrous sodium sulfate
14. concentrationfollowed by concentration under reduced pressure
15. customThe residue was purified with a fractionation purification apparatus (Biotage, ethyl acetate:hexane=2:98-3:7)
16. stirringThe obtained mixture was stirred at 90° C. for 4 hours
17. concentrationThereafter, the reaction solution was concentrated under reduced pressure
18. customthe residue was then purified with a fractionation purification apparatus (Biotage, ethyl acetate:hexane=1:4-4:1)

ORD record

ord-53c92b0603ab4a419af6d2a3ab17f84f

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08648103B2