Reaktion #674304

Reaktionsgleichung

4-(benzyloxy)cyclohexanecarboxylic acid

triethylamine

ethyl chloroformate

→

4-(benzyloxy)cyclohexanecarboxamide

Ausbeute 96.9%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedried 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
   Sonstigeput into the fridge (−20° C.) overnight
4. 4
   Temperaturwarm to room temperature
5. 5
   workup.ADDITIONH2O (100 mL) was added
6. 6
   SonstigeThe layer was separated
7. 7
   Extraktionthe aqueous phase was extracted with DCM (3×100 mL)
8. 8
   WaschenThe combined organic solution was washed with brine (50 mL)
9. 9
   Trocknendried over anhydrous Na2SO4
10. 10
    Einengenconcentrated

Vorschrift

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.

Quelle