反応 #43409

反応方程式

1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

1,1-dimethylethyl [2-[1-(ethyloxy)ethenyl]-5-fluoro-6-(methyloxy)-3-pyridinyl]carbamate

acetonitrile

sodium bicarbonate

sodium bicarbonate

→

1,1-Dimethylethyl [5-fluoro-2-(fluoroacetyl)-6-(methyloxy)-3-pyridinyl]carbamate

溶媒

water

反応条件

後処理

1. 1
   workup.ADDITIONAfter the addition the mixture
2. 2
   workup.STIRRINGstirred for 10 minutes
3. 3
   抽出extracted with ethyl acetate (3×200 ml)
4. 4
   乾燥The combined organic extracts were dried over magnesium sulphate
5. 5
   その他evaporated
6. 6
   その他The residue was chromatographed
7. 7
   洗浄eluting with 0-50% dichloromethane in hexane affording the product as a white solid (3.72 g, 57%)

実験手順

A mixture of 1,1-dimethylethyl [2-[1-(ethyloxy)ethenyl]-5-fluoro-6-(methyloxy)-3-pyridinyl]carbamate (6.72 g, 21.54 mmol), acetonitrile (70 ml), and saturated aqueous sodium bicarbonate solution (15 ml) was treated portionwise over 5 minutes at 0° C. under argon with [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™) (8.9 g, 25.05 mmol). After the addition the mixture was stirred at room temperature for 0.5 hour then treated with saturated aqueous sodium bicarbonate solution (50 ml), stirred for 10 minutes, then diluted with water (100 ml) and extracted with ethyl acetate (3×200 ml). The combined organic extracts were dried over magnesium sulphate and evaporated. The residue was chromatographed eluting with 0-50% dichloromethane in hexane affording the product as a white solid (3.72 g, 57%).

出典