反応 #74430

反応方程式

(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

溶媒

DMF

反応条件

後処理

1. 1
   その他The mixture was partitioned between diethyl ether and water
2. 2
   その他The organic portion was separated
3. 3
   洗浄washed with brine
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The residue was purified by flash column chromatography (0 to 5% of EtOAc in hexanes)

実験手順

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.

出典