Reacción #674304

Ecuación de reacción

4-(benzyloxy)cyclohexanecarboxylic acid

triethylamine

ethyl chloroformate

→

4-(benzyloxy)cyclohexanecarboxamide

Rendimiento 96.9%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrodried NH3 was bubbled rapidly into the liquid for 20 min
2. 2
   workup.STIRRINGThe mixture was stirred at −15° C. for 30 min
3. 3
   Otroput into the fridge (−20° C.) overnight
4. 4
   Temperaturawarm to room temperature
5. 5
   workup.ADDITIONH2O (100 mL) was added
6. 6
   OtroThe layer was separated
7. 7
   Extracciónthe aqueous phase was extracted with DCM (3×100 mL)
8. 8
   LavadoThe combined organic solution was washed with brine (50 mL)
9. 9
   Secadodried over anhydrous Na2SO4
10. 10
    Concentraciónconcentrated

Procedimiento

To a solution of 4-(benzyloxy)cyclohexanecarboxylic acid (5.4 g, 23 mmol, 1.0 equiv) and triethylamine (4.82 mL, 34.57 mmol, 1.5 equiv) in DCM (dry, 40 mL) was added ethyl chloroformate (3.0 mL, 31.1 mmol, 1.35 equiv) dropwise between −20 and −10° C. under N2. The white precipitate appeared. The mixture was stirred at about −15° C. for 10 min, dried NH3 was bubbled rapidly into the liquid for 20 min. The mixture was stirred at −15° C. for 30 min, then put into the fridge (−20° C.) overnight. The flask was released the pressure and warm to room temperature. H2O (100 mL) was added. The layer was separated and the aqueous phase was extracted with DCM (3×100 mL). The combined organic solution was washed with brine (50 mL), dried over anhydrous Na2SO4, concentrated to give 5.2 g (96.7%) of 4-(benzyloxy)cyclohexanecarboxamide as a off-white solid.

Fuente