Reaction #1121758

Reaction equation

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

Imidazole

triethylchlorosilane

→

titled compound

Yield 95.0%

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

Yield 95.0%

Solvents

ethyl acetate

Conditions

Workup

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

Procedure

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