Réaction #631987

Équation de réaction

HCl

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

3-N,N-dimethylaminobenzoic acid

DCC

→

product

Rendement 68.0%

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

Rendement 68.0%

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source