Reaktion #1121758

Reaktionsgleichung

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

Imidazole

triethylchlorosilane

→

titled compound

Ausbeute 95.0%

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

Ausbeute 95.0%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solution was placed in a nitrogen purged flask
2. 2
   Temperaturto warm to room temperature
3. 3
   FiltrationAfter filtration
4. 4
   Waschenthe filtrate was washed with a saturated sodium bicarbonate solution
5. 5
   Trocknena brine solution, respectively, dried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated

Vorschrift

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).

Quelle