Reacción #3498

Ecuación de reacción

water

sodium hydride

methyl N-methoxycarbamate

propargyl bromide

→

methyl N-methoxy-N-propargylcarbamate

Rendimiento 58.7%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawhile being cooled with ice
2. 2
   TemperaturaThe mixture was heat-refluxed for 4 hours
3. 3
   workup.ADDITIONwas added to the reaction solution
4. 4
   Extracciónthe mixture was extracted with ethyl acetate
5. 5
   OtroThe extract was dried
6. 6
   Concentraciónconcentrated
7. 7
   Otropurified by silica gel column chromatography

Procedimiento

0.43 g of sodium hydride (60% in oil) was suspended in 10 ml of tetrahydrofuran, and 1.0 g of methyl N-methoxycarbamate and 1.36 g of propargyl bromide were added to the suspension in this order while being cooled with ice. The mixture was heat-refluxed for 4 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried, concentrated and purified by silica gel column chromatography to obtain 0.8 g of methyl N-methoxy-N-propargylcarbamate.

Fuente