Реакция #1121758

Уравнение реакции

(R)-2-ethoxycarbonylmethyl-4-hydroxy-2-cyclopenten-1-one

Imidazole

triethylchlorosilane

→

titled compound

Выход 95.0%

(R)-2-ethoxycarbonylmethyl-4-triethylsilyloxy-2-cyclopenten-1-one

Выход 95.0%

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   Другоеthe solution was placed in a nitrogen purged flask
2. 2
   Температураto warm to room temperature
3. 3
   ФильтрацияAfter filtration
4. 4
   Промывкаthe filtrate was washed with a saturated sodium bicarbonate solution
5. 5
   Сушкаa brine solution, respectively, dried over anhydrous magnesium sulfate
6. 6
   Концентрированиеconcentrated

Методика

25 g of (R)-2-ethoxycarbonylmethyl-4-hydroxy-2-cyclopenten-1-one (5 g, 98% e.e.) was dissolved in ethyl acetate and the solution was placed in a nitrogen purged flask. Imidazole (13.87 g, 204 mmol) was added. The solution was cooled to 0° C. and triethylchlorosilane (26.6 g, 176 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for another 15 hours. After filtration, the filtrate was washed with a saturated sodium bicarbonate solution and a brine solution, respectively, dried over anhydrous magnesium sulfate, and concentrated to obtain the titled compound (38.5 g, 95%). [α]D: +27.8° (c 1.0, CH3CN).

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