Reaction #674304

Reaction equation

4-(benzyloxy)cyclohexanecarboxylic acid

triethylamine

ethyl chloroformate

→

4-(benzyloxy)cyclohexanecarboxamide

Yield 96.9%

Solvents

DCM

Conditions

Workup

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

Procedure

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