反应详情

Combine (S)-2-(4-fluorophenyl)pent-4-enoic acid, N-methyl amide (3.1 g, 14.96 mmol) and tetrahydrofuran (35 mL). Cool in an ice bath, add a solution of lithium aluminum hydride (35 mL, 1.0 M in tetrahydrofuran, 35 mmol). After the addition is complete, heat the reaction mixture to reflux. After 2.5 hours, cool in an ice bath and carefully quench with water (1.3 mL), an aqueous 15% sodium hydroxide solution (1.3 mL), and then water (4 mL). Dilute the quenched reaction mixture with diethyl ether (75 mL), add MgSO4, and stir. After 1 hour, filter through celite and rinse the solids with dichloromethane. Evaporate the filtrate in vacuo to give (S)-N-methyl-(2-(4-fluorophenyl)pent-4-enyl)amine: Rf =0.47 (silica gel, 18.5/1.5/0.2 dichloromethane/methanol/concentrated aqueous ammonia).

1. temperatureCool in an ice bath
2. additionAfter the addition
3. temperatureheat the reaction mixture
4. temperatureto reflux
5. temperaturecool in an ice bath
6. customcarefully quench with water (1.3 mL)
7. additionDilute
8. customthe quenched reaction mixture with diethyl ether (75 mL)
9. waitAfter 1 hour
10. filtrationfilter through celite
11. washrinse the solids with dichloromethane
12. customEvaporate the filtrate in vacuo