Sodium Cyanide → 2-Amino-2-(fluoromethyl)-5-methoxypentanenitrile

温度

-30 °C

Under an atmosphere of nitrogen, 3-methoxypropyl magnesium chloride is prepared from 3-methoxy-1-chloropropane (5.43 g, 50 mmol, prepared according to Haworth and Perkin, Chem. Zentralblatt II 1271 (1912) and magnesium turnings (1.22 g, 50 mmol) in dry THF (50 ml). The mixture is heated under reflux for 3 hours, then cooled to -30° C. and a solution of fluoroacetonitrile (2.95 g, 50 mmol) in THF (30 ml) is added during 20 minutes. After keeping the mixture at -30° C. for 1/2 hour more, a solution of sodium cyanide (4.9 g, 100 mmol) and ammonium chloride (8.09 g, 150 mmol) in water (100 mL), previously cooled to 0° C., is added and the mixture is stirred for 3/4 hours at room temperature. After saturating with sodium chloride, the THF layer is separated and the aqueous phase is extracted twice with ether. After drying (Na2SO4), the combined organic extracts are evaporated to give 2-fluoromethyl-2-amino-5-methoxyvaleronitrile (4.0 g) as a brown oil.

1. customprepared
2. temperatureThe mixture is heated
3. temperatureunder reflux for 3 hours
4. customat -30° C.
5. customfor 1/2 hour
6. additionis added
7. concentrationAfter saturating with sodium chloride
8. customthe THF layer is separated
9. extractionthe aqueous phase is extracted twice with ether
10. dry with materialAfter drying (Na2SO4)
11. customthe combined organic extracts are evaporated

ORDレコード

ord-63f2d3c1f3a04870a6a268b8fcf77aca

出典データセット

uspto-grants-1982_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04330559