반응 #43409

반응 방정식

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

용매

water

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition the mixture
2. 2
   workup.STIRRINGstirred for 10 minutes
3. 3
   추출extracted with ethyl acetate (3×200 ml)
4. 4
   건조The combined organic extracts were dried over magnesium sulphate
5. 5
   기타evaporated
6. 6
   기타The residue was chromatographed
7. 7
   세척eluting with 0-50% dichloromethane in hexane affording the product as a white solid (3.72 g, 57%)

실험 절차

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%).

출처