Reacción #1121758

Ecuación de reacción

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

Imidazole

triethylchlorosilane

→

titled compound

Rendimiento 95.0%

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

Rendimiento 95.0%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solution was placed in a nitrogen purged flask
2. 2
   Temperaturato warm to room temperature
3. 3
   FiltraciónAfter filtration
4. 4
   Lavadothe filtrate was washed with a saturated sodium bicarbonate solution
5. 5
   Secadoa brine solution, respectively, dried over anhydrous magnesium sulfate
6. 6
   Concentraciónconcentrated

Procedimiento

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).

Fuente