Reaktion #2326399

Reaktionsgleichung

HCl

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

3-N,N-dimethylaminobenzoic acid

DCC

→

product

Ausbeute 68.0%

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

Ausbeute 68.0%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle