Reacción #631987

Ecuación de reacción

HCl

3-hydroxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone

3-N,N-dimethylaminobenzoic acid

DCC

→

product

Rendimiento 68.0%

1-methyl-3-oxo-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)propyl 3-(dimethyl-amino)benzoate

Rendimiento 68.0%

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted twice with ether
2. 2
   Lavadowashed with water, saturated aqueous NaHCO3
3. 3
   SecadoFinally, the organic phases were dried over Na2SO4
4. 4
   Concentraciónconcentrated at 50-60°/0.03 mbar) and
5. 5
   Otropurified by flash-chromatography over SiO2 (cyclohexane/AcOEt=97:3)

Procedimiento

To a solution of 3-hydroxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone (4.00 g, 92% pure, 17.5 mmol), 3-N,N-dimethylaminobenzoic acid (3.13 g, 19.0 mmol), and DMAP (1.85 g, 15.2 mmol) in CH2Cl2 (50 ml) was added N,N′-dicyclohexylcarbodiimine (DCC) (4.31 g, 20.9 mmol) in CH2Cl2 (15 ml). The reaction medium was stirred at room temperature for 70 h. Then, the mixture was acidified with concentrated HCl and extracted twice with ether and washed with water, saturated aqueous NaHCO3 and then with saturated aqueous NaCl. Finally, the organic phases were dried over Na2SO4, concentrated at 50-60°/0.03 mbar) and purified by flash-chromatography over SiO2 (cyclohexane/AcOEt=97:3). 4.20 g of product were thus obtained (yield: 68%).

Fuente