反応 #631987

反応方程式

HCl

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

3-N,N-dimethylaminobenzoic acid

DCC

→

product

収率 68.0%

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

収率 68.0%

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

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

実験手順

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%).

出典