反応 #631986

反応方程式

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

NEt3

dimethylamino pyridine

benzoylchloride

HCl

→

product

収率 77.2%

1-methyl-3-oxo-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)propyl Benzoate

収率 77.2%

溶媒

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), NEt3 (3.2 ml, 22.85 mmol) and dimethylamino pyridine (DMAP) (400 mg) in CH2Cl2 (100 ml) was added benzoylchloride (2.43 ml, 20.94 mmol). The reaction medium was stirred for 65 h at room temperature. Then, the mixture was acidified with 5% aqueous 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). 4.25 g of product were thus obtained (yield: 73%).

出典