Réaction #1121758

Équation de réaction

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

Imidazole

triethylchlorosilane

→

titled compound

Rendement 95.0%

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

Rendement 95.0%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Autrethe solution was placed in a nitrogen purged flask
2. 2
   Températureto warm to room temperature
3. 3
   FiltrationAfter filtration
4. 4
   Lavagethe filtrate was washed with a saturated sodium bicarbonate solution
5. 5
   Séchagea brine solution, respectively, dried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated

Mode opératoire

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).

Source