تفاعل #1121758

معادلة التفاعل

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

Imidazole

triethylchlorosilane

→

titled compound

المردود 95.0%

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

المردود 95.0%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solution was placed in a nitrogen purged flask
2. 2
   درجة الحرارةto warm to room temperature
3. 3
   ترشيحAfter filtration
4. 4
   غسيلthe filtrate was washed with a saturated sodium bicarbonate solution
5. 5
   تجفيفa brine solution, respectively, dried over anhydrous magnesium sulfate
6. 6
   تركيزconcentrated

الإجراء التجريبي

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).

المصدر