Реакция #631987

Уравнение реакции

HCl

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

3-N,N-dimethylaminobenzoic acid

DCC

→

product

Выход 68.0%

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

Выход 68.0%

Растворители

CH2Cl2

CH2Cl2

Условия реакции

Обработка

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

Методика

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%).

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