Hydrochloric Acid → HCID 22221148, compound

To a solution of 3-(5-phenyl-4-isoxazolyl)propan-1-ol (15.00 g) and triethylamine (21.0 ml) in ethyl acetate (500 ml) was gently added methanesulfonyl chloride (9.0 ml) at 0° C., and the mixture was stirred at room temperature overnight. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. A mixture of the residue, sodium cyanide (7.33 g), sodium iodide (13.48 g) and N,N-dimethylformamide (150 ml) was stirred at 70° C. for 5 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 4-(5-phenyl-4-isoxazolyl)butyronitrile (13.47 g, yield 86%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). NMR (CDCl3) δ: 1.91–2.09 (2H, m), 2.36–2.46 (2H, m), 2.78–2.94 (2H, m), 7.44–7.58 (3H, m), 7.64–7.74 (2H, m), 8.22 (1H, s).

1. customat 0° C.
2. extractionthe mixture was extracted with ethyl acetate
3. washThe ethyl acetate layer was washed with saturated brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. additionA mixture of the residue, sodium cyanide (7.33 g), sodium iodide (13.48 g) and N,N-dimethylformamide (150 ml)
7. stirringwas stirred at 70° C. for 5 hr
8. additionThe reaction mixture was poured into water
9. extractionthe mixture was extracted with ethyl acetate
10. washThe ethyl acetate layer was washed with saturated brine
11. dry with materialdried (MgSO4)
12. concentrationconcentrated

ORD record

ord-f3de2c69751b4ed298b76c813e8f92dc

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07022725B2