Réaction #1605782

Équation de réaction

pyridine

pyridine

triphosgene

diethylamine

2,3,6-trimethylcyclohexanol

→

desired product

Rendement 51.8%

Diethyl-carbamic acid 2,3,6-trimethyl-cyclohexyl ester

Rendement 51.8%

Solvants

dichlormethane

dichlormethane

dichlormethane

Conditions de réaction

Traitement

1. 1
   Autreto come to ambient temperature
2. 2
   Autrequenched with water
3. 3
   AutreAfter separation of the phases
4. 4
   Extractionthe water phase was extracted once with dichlormethane
5. 5
   Concentrationthe combined organic phases were concentrated
6. 6
   workup.DISTILLATIONThe raw product was purified by distillation and column chromatography

Mode opératoire

4.27 g (30 mmol) of 2,3,6-trimethylcyclohexanol were placed with 110 ml dichlormethane in a 250 ml vessel at room temperature and 3.08 g (39 mmol) of pyridine were added. The reaction mixture was cooled to 0° C. and 3.56 g (12 mmol) of triphosgene in 15 ml dichlormethane were added dropwise. After five minutes 2.37 g (30 mmol) pyridine were added. Subsequently, 2.19 g (30 mmol) of diethylamine in 15 ml dichlormethane were added dropwise, the resulting mixture was allowed to come to ambient temperature and then quenched with water. After separation of the phases, the water phase was extracted once with dichlormethane and the combined organic phases were concentrated. The raw product was purified by distillation and column chromatography to yield 1.5 g of the desired product as a mixture of isomers with a purity of 99.4%.

Source