反応 #159447

反応方程式

3-(5-bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione

sodium iodide

hexamethyldisilazane

trans-N,N′-dimethylcyclohexane-1,2-diamine

→

3-(2-ethyl-5-iodophenyl)bicyclo[3.2.1]-octane-2,4-dione

収率 100.0%

溶媒

dioxane

反応条件

後処理

1. 1
   その他After purging with nitrogen the mixture
2. 2
   温度The mixture is cooled to room temperature
3. 3
   その他quenched with 2M hydrochloric acid
4. 4
   抽出extracted with dichloromethane (×2)
5. 5
   洗浄washed with saturated aqueous sodium metabisulfite
6. 6
   乾燥dried over magnesium sulfate
7. 7
   ろ過then filtered
8. 8
   濃縮The filtrate is concentrated in vacuo
9. 9
   その他purified by flash column chromatography (20% to 100% ethyl acetate/hexane eluant ratio)

実験手順

To a microwave vial is added 3-(5-bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione (1.00 g, 3.11 mmol), sodium iodide (0.93 g, 6.23 mmol), hexamethyldisilazane (0.45 g, 3.11 mmol), copper(I) iodide (0.03, 0.15 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (0.044 g, 0.31 mmol) then degassed dioxane (5 ml). After purging with nitrogen the mixture is heated at 180° C. for 1 hour under microwave irradiation. The mixture is cooled to room temperature, quenched with 2M hydrochloric acid and extracted with dichloromethane (×2). Organic fractions are combined, washed with saturated aqueous sodium metabisulfite, dried over magnesium sulfate then filtered. The filtrate is concentrated in vacuo, then purified by flash column chromatography (20% to 100% ethyl acetate/hexane eluant ratio) to afford 3-(2-ethyl-5-iodophenyl)bicyclo[3.2.1]-octane-2,4-dione (1.14 g, 100%) as a white solid.

出典