반응 #2267151

반응 방정식

product

[(3R)-3-(3-Furanyl)-3-hydroxypropyl]carbamic acid 1,1-dimethylethyl ester

4-chloro-2,5-difluorobenzonitrile

sodium hydride

→

title compound

수율 73.0%

[(3R)-3-(5-Chloro-2-cyano-4-fluorophenoxy)-3-(3-furanyl)propyl]-carbamic acid 1,1-dimethylethyl ester

수율 73.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   기타then quenched with aqueous saturated ammonium chloride solution (30 ml)
2. 2
   추출extracted with ethyl acetate (3×60 ml)
3. 3
   세척The combined organic extracts were washed with water (3×20 ml)
4. 4
   건조dried (sodium sulphate)
5. 5
   기타evaporated iii vacuo
6. 6
   기타The residue was chromatographed on flash silica
7. 7
   세척eluting with hexane:ethyl acetate (3:1)

실험 절차

The product of step (b) (277 mg, 1.15 mmol) and 4-chloro-2,5-difluorobenzonitrile (199 mg, 1.15 mmol) were dissolved in dimethylformamide (10 ml) and sodium hydride (60%, 48 mg, 1.2 mmol) added in one portion. The reaction was stirred for 2 h at room temperature then quenched with aqueous saturated ammonium chloride solution (30 ml) and extracted with ethyl acetate (3×60 ml). The combined organic extracts were washed with water (3×20 ml), dried (sodium sulphate) and evaporated iii vacuo. The residue was chromatographed on flash silica, eluting with hexane:ethyl acetate (3:1), to give the title compound as a white crystalline solid (330 mg, 73%).

출처