반응 #927237

반응 방정식

sodium hydride

trifluoroacetamide

8-iodo-1-octyne

ammonium chloride

→

8-trifluoroacetamido-1-octyne

수율 79.5%

용매

DMF

DMF

ether

반응 조건

후처리

1. 1
   workup.ADDITIONwas added portionwise with ice cooling
2. 2
   건조The ether layer was dried over magnesium sulfate
3. 3
   농축concentrated under reduced pressure
4. 4
   기타the resulting residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate mixed solvent)
5. 5
   기타crystallized from hexane

실험 절차

To a solution of sodium hydride (60% oil, 9.82 g, 245 mmol) in DMF (200 ml), trifluoroacetamide (34.7 g, 307 mmol) divided into 10 portion was added portionwise with ice cooling. Then, the reaction mixture was added with a solution of 8-iodo-1-octyne (14.5 g, 61.4 mmol) in DMF (60 ml), and stirred at room temperature for two hours. The reaction mixture was added with saturated aqueous ammonium chloride (400 ml) and ether (400 ml) for extraction. The ether layer was dried over magnesium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate mixed solvent), and crystallized from hexane to afford 10.8 g of 8-trifluoroacetamido-1-octyne (yield; 79.3%).

출처