تفاعل #74430

معادلة التفاعل

(1R,2S,4R,5S)-5-(benzyloxy)bicyclo[2.2.1]heptan-2-ol

tert-butylchlorodiphenylsilane

imidazole

→

title compound

((1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-yloxy)(tert-butyl)diphenylsilane

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was partitioned between diethyl ether and water
2. 2
   أخرىThe organic portion was separated
3. 3
   غسيلwashed with brine
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىThe residue was purified by flash column chromatography (0 to 5% of EtOAc in hexanes)

الإجراء التجريبي

To a solution of (1R,2S,4R,5S)-5-(benzyloxy)bicyclo[2.2.1]heptan-2-ol (4.20 g, 19.2 mmol) in DMF (10 mL) was added tert-butylchlorodiphenylsilane (6.00 mL, 23.1 mmol) and imidazole (3.27 g, 48.1 mmol). The resulting mixture was stirred at ambient temp. overnight. The mixture was partitioned between diethyl ether and water. The organic portion was separated, washed with brine, and concentrated in vacuo. The residue was purified by flash column chromatography (0 to 5% of EtOAc in hexanes) to give the title compound as a colorless oil.

المصدر