反应 #631987

反应方程式

HCl

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

3-N,N-dimethylaminobenzoic acid

DCC

→

product

收率 68.0%

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

收率 68.0%

溶剂

CH2Cl2

CH2Cl2

反应条件

后处理

1. 1
   萃取extracted twice with ether
2. 2
   洗涤washed with water, saturated aqueous NaHCO3
3. 3
   干燥Finally, the organic phases were dried over Na2SO4
4. 4
   浓缩concentrated at 50-60°/0.03 mbar) and
5. 5
   其他purified by flash-chromatography over SiO2 (cyclohexane/AcOEt=97:3)

实验过程

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%).

来源