Реакция #631986

Уравнение реакции

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

NEt3

dimethylamino pyridine

benzoylchloride

HCl

→

product

Выход 77.2%

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

Выход 77.2%

Растворители

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), 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%).

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