Réaction #674304

Équation de réaction

4-(benzyloxy)cyclohexanecarboxylic acid

triethylamine

ethyl chloroformate

→

4-(benzyloxy)cyclohexanecarboxamide

Rendement 96.9%

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   Autredried 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
   Autreput into the fridge (−20° C.) overnight
4. 4
   Températurewarm to room temperature
5. 5
   workup.ADDITIONH2O (100 mL) was added
6. 6
   AutreThe layer was separated
7. 7
   Extractionthe aqueous phase was extracted with DCM (3×100 mL)
8. 8
   LavageThe combined organic solution was washed with brine (50 mL)
9. 9
   Séchagedried over anhydrous Na2SO4
10. 10
    Concentrationconcentrated

Mode opératoire

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.

Source