Reacción #57359

Ecuación de reacción

methyl 4,4-dimethoxy-butyrate

N,O-dimethylhydroxylamine HCl

isopropylmagnesiumchloride

→

4,4,N-Trimethoxy-N-methyl-butyramide

Rendimiento 100.2%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturamaintaining the temperature below −20° C
2. 2
   Otrothe reaction mixture is quenched with 50 mL of water
3. 3
   Extracciónextracted with 3×80 mL of EtOAc
4. 4
   SecadoThe combined organic layers is dried over Na2SO4
5. 5
   Filtraciónfiltered through a short silica gel pluge
6. 6
   ConcentraciónThe solution is concentrated

Procedimiento

To a solution of methyl 4,4-dimethoxy-butyrate(4.99 g, 30.8 mmol) and N,O-dimethylhydroxylamine HCl(4.65 g, 47.68 mmol) in 60 mL of THF at −20° C., is added isopropylmagnesiumchloride(46 mL, 92.28 mmol, 2.0M in THF) maintaining the temperature below −20° C. After stirring at −10° C. for 30 min, the reaction mixture is quenched with 50 mL of water and extracted with 3×80 mL of EtOAc. The combined organic layers is dried over Na2SO4 and filtered through a short silica gel pluge. The solution is concentrated to give 4,4,N-Trimethoxy-N-methyl-butyramide(5.9 g, 99%) as pale liquid. M/Z=191.0

Fuente